EP1231839A2 - Herbicide means with acylated amino phenyl sulfonyl carbamide - Google Patents

Herbicide means with acylated amino phenyl sulfonyl carbamide

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Publication number
EP1231839A2
EP1231839A2 EP00981250A EP00981250A EP1231839A2 EP 1231839 A2 EP1231839 A2 EP 1231839A2 EP 00981250 A EP00981250 A EP 00981250A EP 00981250 A EP00981250 A EP 00981250A EP 1231839 A2 EP1231839 A2 EP 1231839A2
Authority
EP
European Patent Office
Prior art keywords
herbicides
plants
group
radicals
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP00981250A
Other languages
German (de)
French (fr)
Other versions
EP1231839B1 (en
Inventor
Erwin Hacker
Hermann Bieringer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Aventis CropScience GmbH
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Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Priority to SI200030155T priority Critical patent/SI1231839T1/en
Publication of EP1231839A2 publication Critical patent/EP1231839A2/en
Application granted granted Critical
Publication of EP1231839B1 publication Critical patent/EP1231839B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention is in the technical field of crop protection agents which are used against harmful plants e.g. can be used in plant crops and contain a combination of at least two herbicides as active ingredients.
  • R) 1 1 hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
  • R 2 is hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
  • Methyl, R 3 hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C 2 -C 4 ) alkenoxy, (C 2 -C 4 ) alkynoxy,
  • C 4 ) alkoxy and (CC 4 ) alkylsulfonyl is substituted, preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl,
  • C 4 ) alkylthio is substituted, in particular X and Y are each methoxy, and Z is CH or N, in particular CH.
  • the effectiveness of these herbicides against harmful plants in plant crops is at a high level, but generally depends on the application rate, the particular form of preparation, the harmful plants to be controlled or the range of harmful plants, the climate and soil conditions, etc. Another criterion is the duration of action or the rate of degradation of the herbicide. If necessary, changes in the sensitivity of harmful plants that may occur with extended use of the herbicides or geographically limited must also be taken into account. Loss of activity in individual harmful plants can only be compensated for to a limited extent by higher amounts of herbicides, for. B. because this often worsens the selectivity of the herbicides or does not result in an improvement in activity, even with a higher application rate. In some cases, the selectivity in cultures can be improved by adding safeners.
  • a lower application rate not only reduces the amount of an active ingredient required for the application, but generally also reduces the amount of formulation auxiliaries required. Both reduce the economic effort and improve the ecological compatibility of herbicide treatment.
  • One way to improve the application profile of a herbicide is to combine the active ingredient with one or more other active ingredients. However, phenomena of physical and biological incompatibility often occur with the combined use of several active ingredients, e.g. B. lack of stability in a co-formulation, decomposition of an active ingredient or antagonism of the active ingredients.
  • combinations of active ingredients with a favorable activity profile, high stability and, as far as possible, synergistically enhanced action are desired, which allow a reduction in the application rate compared to the individual application of the active ingredients to be combined.
  • the invention thus relates to herbicide combinations with an effective content of components (A) and (B), wherein
  • R) 1 hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular methyl
  • R 2 is hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
  • Methyl, R 3 hydrogen, (C r C 4 ) alkyl, (CC 4 ) alkoxy, (C 2 -C 4 ) alkenoxy, (C 2 -C 4 ) alkynoxy, (C 3 -C 6 ) cycloalkyl, each of which 5 last-mentioned radicals unsubstituted or substituted by one or more radicals from the group halogen, cyano, (CC 4 ) alkoxy and (CC 4 ) alkylsulfonyl, preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy or Ethoxy, preferably hydrogen, methyl or methoxy, especially hydrogen, one of the radicals X and Y halogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, each of the latter three
  • (B) means one or more herbicides from the group of the compounds consisting of (indication with the "common name” and the reference point from "The Pesticide Manual” 11th Ed., British Crop Protection Council 1997, abbreviated "PM")
  • (B1) selectively herbicides active in some dicotyledon crops against monocotyledonous and dicotyledonous harmful plants, selected from the group consisting of:
  • (B2) selectively in some dicotyledon crops, herbicides active predominantly against dicotyledonous harmful plants, selected from the group consisting of (B2.1) Desmedipham (PM, pp. 349-350), ie, N- [3-
  • Application ratio A: B 1: 800 - 4: 1, preferably 1: 200 - 1: 1);
  • the herbicide combinations according to the invention have a herbicidally active content of components A and B and can contain further components, for.
  • the herbicide combinations according to the invention have synergistic effects.
  • the synergistic effects are observed when the active ingredients (A) and (B) are applied together, but can often also occur with a time delay Application (splitting) can be determined.
  • Preferred is the simultaneous or prompt application of the active compounds of the herbicide combination according to the invention.
  • the synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency with the same application rate, the control of previously unrecognized types (gaps), an extension of the application period and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and more environmentally friendly weed control systems.
  • the combinations of (A) + (B) according to the invention enable synergistic increases in activity which go far and unexpectedly beyond the effects which are achieved with the individual active compounds (A) and (B).
  • the herbicidal combination partners from group (B1) act against mono- and dicotyledonous harmful plants.
  • the herbicidal combination partners from group (B2) mainly act against dicotyledonous harmful plants, but can also be effective in some cases against monocolyte harmful plants.
  • the herbicidal combination partners from group (B3) mainly act against monocotyledonous harmful plants, but in some cases they can also be effective against dicotyledonous harmful plants.
  • the formula (I) mentioned comprises all stereoisomers and their mixtures, in particular also racemic mixtures, and - insofar as enantiomers are possible - the biologically active enantiomer in each case.
  • Compounds of formula (I) and their Production are described, for example, in WO 95/29899.
  • active substances of the formula (I) are compounds of the formula (A1) and their salts
  • active substances of the formula (I) are compounds of the formula (A2) and their salts
  • active substances of the formula (I) are compounds of the formula (A3) and their salts
  • R 4 methoxy, chlorine or methyl, preferably the compounds (A3.1) to (A3.6)
  • the herbicides of formula (I) and their salts inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants.
  • the application rates are generally lower, for example in the range from 0.5 to 120 g ai / ha, preferably 2 to 80 g ai / ha Active ingredients can usually be formulated as water-soluble wettable powder (WP), water-dispersible granulate (WDG), water-emulsifiable granulate (WEG), suspoemulsion (SE) or oil suspension concentrate (SC).
  • WP water-soluble wettable powder
  • WDG water-dispersible granulate
  • WEG water-emulsifiable granulate
  • SE suspoemulsion
  • SC oil suspension concentrate
  • the application rate ratios A: B used in general are given above and denote the weight ratio of the two components A and B to one another.
  • a safener from certain application rates in order to reduce or avoid damage to the crop.
  • suitable safeners are those which, in combination with sulfonylurea herbicides, preferably phenylsulfonylureas Develop safener effect.
  • Suitable safeners are known from WO-A-96/14747 and the literature cited therein.
  • EP-A-191 736 or EP-A-0 492 366 Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid, preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5- Chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.
  • active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type e.g.
  • esters 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop), MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (dicamba) ,
  • Dichloro-2-phenylpyrimidine i) Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners
  • O- (1, 3-dioxolan-2-ylmethyl) oxime which is known as a seed dressing safener against damage to metolachlor
  • Metolachlor is known, I) active substances of the thiazole carboxylic acid ester type, which are known as seed dressings, such as
  • Seed dressings are known, e.g.
  • Naphthalenedicarboxylic anhydride which acts as a seed dressing safener against corn
  • n) active compounds of the chromanacetic acid dehvatre type such as e.g.
  • the active ingredients (A) are suitable, if appropriate in the presence of safeners, for controlling harmful plants in crops, for example in economically important crops such as cereals (for example wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, Rapeseed, cotton and soy. Of particular interest is the use in dicotyledon crops such as sugar beet, rapeseed, cotton and soy. These cultures are also preferred for the combinations (A) + (B).
  • Herbicides active against harmful plants selected from the group consisting of
  • soybean selective herbicides selected from the group consisting of (B1.15) trifluralin (PM, pp. 1248-1250), i.e. ⁇ , ⁇ , ⁇ -trifluoro-2,6-dinitro-
  • Herbicides active on harmful plants selected from the group consisting of: a) herbicides selective in sugar beet selected from the group consisting of
  • B2.7 pyrithiobac and its salts, e.g. B. the sodium salt, (PM, pp. 1073-1075), d. H. 2-chloro-6- (4,6-dimethoxypyrimidin-2-ylthio) benzoic acid sodium salt;
  • soybean selective herbicides selected from the group consisting of (B2.8) Oxyfluorfen (PM, pp. 919-921), ie 2-chloro- ⁇ , ⁇ , ⁇ -trifluoro-p-tolyl
  • esters such as the pentyl ester; (B2.11) 2,4-DB (PM, pp. 337-339), i.e. 4- (2,4-dichlorophenoxy) butyric acid, and its esters and salts; (B2.12) Diclosulam (see AG CHEM New Compound Review, Vol. 17,
  • Herbicides active against harmful plants selected from the group consisting of
  • Tepraloxydim (DE 4222261), i.e. 2- [1 - [[[(2E) -3-chloro-2-propenyl] oxy] imino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1 -one;
  • Herbicide combinations of one or more compounds (A) with one or more compounds of group (B1) or (B2) or (B3) are preferred.
  • Combinations of compounds (A) with one or more compounds (B) according to the scheme are further preferred:
  • combinations according to the invention can be used together with other agrochemical active ingredients, for example from the group of safeners, fungicides, insecticides and plant growth regulators or additives and formulation auxiliaries customary in crop protection.
  • Additives include fertilizers and dyes.
  • the combinations according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence. Use in the post-emergence process or in the early post-sowing pre-emergence process is preferred.
  • the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp ., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., on the annual side, and convolvulus, cirsium, rumex and artemisia in the perennial weeds.
  • the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the herbicidal compositions according to the invention are notable for a rapid onset and long-lasting herbicidal action.
  • the rain resistance of the active ingredients in the combinations according to the invention is generally favorable.
  • a particular advantage is that the effective dosages of compounds (A) and (B) used in the combinations can be set so low that their soil effect is optimally low. This means that their use is not only possible in sensitive crops, but groundwater contamination is practically avoided.
  • the combination of active substances according to the invention enables a considerable reduction in the necessary application rate of the active substances.
  • the combinations according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.
  • some of the agents according to the invention have excellent growth-regulating properties in the crop plants. You grab regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, such as by triggering desiccation and stunted growth.
  • they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as losses in the harvest can be reduced or completely prevented.
  • compositions according to the invention for controlling harmful plants can be used in genetically modified crops or crops obtained by mutation selection.
  • crop plants are generally distinguished by special advantageous properties, such as resistance to herbicidal agents or resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients. For example, Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, transgenic crop plants which are resistant to other herbicides, for example to sulfonylureas (EP-A-0257993, US-A-
  • Bacillus thuringiensis toxins (Bt toxins) which the
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense-RNA, a sense-RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically transcripts the above Gene product splits.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
  • the invention also relates to a process for controlling undesirable plant growth, preferably in crops such as cereals (for example wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, particularly preferably in dicotyledons Cultures such as sugar beet, rapeseed, cotton and soy, characterized in that one or several herbicides of type (A) with one or more herbicides of type (B) on the harmful plants, parts of plants, plant seeds or the area on which the plants grow, for example the area under cultivation.
  • crops such as cereals (for example wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, particularly preferably in dicotyledons Cultures such as sugar beet, rapeseed, cotton and soy, characterized in that one or several herbicides of type (A) with one or more herbicides of type
  • the plant cultures can also be genetically modified or obtained by mutation selection and are preferably tolerant of acetolactate synthase (ALS) inhibitors.
  • ALS acetolactate synthase
  • the invention also relates to the use of the new combinations of compounds (A) + (B) for controlling harmful plants, preferably in plant crops.
  • the active compound combinations according to the invention can be present both as mixed formulations of the two components (A) and (B), if appropriate with further agrochemical active compounds, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or as so-called tank mixes joint dilution of the separately formulated or partially separately formulated components with water.
  • the compounds (A) and (B) or their combinations can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified.
  • general formulation options are: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), dispersions based on oil or water, suspoemulsions, dusts (DP), mordants, granules for soil or litter application or water-dispersible granules (WG), ULV formulations, microcapsules or waxes.
  • combinations with other agrochemical active ingredients such as other herbicides, fungicides, insecticides, as well as safeners, fertilizers and / or growth regulators, can be prepared, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or also oleoylmethyltauric acid sodium.
  • ionic or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates
  • Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers).
  • organic solvents for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid ester sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene ethoxylate sorbet, polyoxyethylene ethoxylate or polyoxyethylene ethoxylate.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • SC Suspension concentrates
  • You can, for example, by wet grinding using commercially available bead mills and optionally adding other surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally other surfactants, such as those e.g. already listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be used in the manner customary for the production of fertilizer granules. if desired in a mixture with fertilizers - granulated. Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical formulations usually contain 0.1 to 99
  • the active substance concentration in wettable powders is e.g. about 10 to 95% by weight of the
  • the remainder to 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can e.g. 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating agents and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, preservatives and antifreeze agents. and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and agents which influence the pH or the viscosity.
  • the action of herbicides can be improved by surface-active substances, preferably by wetting agents from the series of alkyl polyglycol ether sulfates, which contain, for example, 10 to 18 carbon atoms and are used in the form of their alkali metal or ammonium salts, but also as a magnesium salt such as C 12 / C 14 fatty alcohol diglycol ether sulfate sodium (Genapol® LRO, Hoechst); see EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988).
  • alkyl polyglycol ether sulfates are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides from the imidazolinone series; see for example EP-A-0502014.
  • the herbicidal effect can also be enhanced by using vegetable oils.
  • vegetable oils is understood to mean oils from oil-producing plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C 10 -C 22 , preferably C 12 -C 20 fatty acids.
  • the C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 fatty acids, in particular with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C 18 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • C 10 -C 22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 fatty acids, such as those contained in oils from oil-producing plant species, or CC 20 alkyl- C 10 C 22 fatty acid esters, such as those obtained by transesterification of the above-mentioned glycerol or glycol C 10 -C 22 - Fatty acid esters with C 1 -C 4 alcohols (for example methanol, ethanol, propanol or butanol) can be obtained.
  • the transesterification can be carried out according to known methods, as described, for example, in the Römpp Chemie Lexikon, 9th edition, volume 2, page 1343, Thieme Verlag Stuttgart.
  • CC ⁇ alkyl-C ⁇ -C ⁇ fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethyl-hexyl esters and dodecyl esters.
  • glycol and glycerol-C 10 -C 22 fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C 10 -C 22 fatty acids, in particular those fatty acids with an even number of carbon atoms, for example erucic acid, lauic acid, palmitic acid and in particular C 18 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils can be used in the herbicidal compositions according to the invention e.g. in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten® (Victorian Chemical Company, Australia, hereinafter called Hasten, main constituent: rapeseed oil ethyl ester), Actirob®B (Novance, France, hereinafter referred to as ActirobB, main constituent: rapeseed oil methyl ester), Rako -Binol® (Bayer AG, Germany, hereinafter called Rako-Binol, main component: rapeseed oil), Renol® (Stefes, Germany, hereinafter referred to as Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinafter referred to as Mero, main component: Rapeseed oil methyl ester) may be included.
  • Hasten® Van
  • the formulations present in the commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground granules or granules for spreading, and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the active compounds can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
  • One possible application is the joint application of the active ingredients in the form of tank mixes, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
  • a common herbicidal formulation of the combination of active compounds (A) and (B) according to the invention has the advantage of being easier to use because the amounts of the components have already been set in the correct ratio to one another.
  • the auxiliaries in the formulation can be optimally coordinated with one another, while a tank mix of different formulations can result in undesired combinations of auxiliaries.
  • a dusting agent is obtained by mixing 10 parts by weight of an active ingredient / active ingredient mixture and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of an active substance / active substance mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium mixes as a wetting and dispersing agent and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (7Triton X 207) and 3 parts by weight Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277EC) are mixed and ground in a attritor to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active substance / active substance mixture, 75 parts by weight of cydohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • a water-dispersible granulate is obtained by adding 75 parts by weight of an active ingredient / active ingredient mixture,
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture,
  • the seeds or rhizome pieces of typical harmful plants were laid out and grown under natural outdoor conditions.
  • the treatment with the agents according to the invention was generally carried out after the emergence of the harmful plants in the 2 to 8 leaf stage in various dosages with a water application rate of the equivalent of 100 to 400 l / ha.

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Abstract

The invention relates to a combination of herbicides. Said combination has a content of components (A) and (B) and is provided with synergistic herbicidal effects: (A) one or more herbicides of formula (I) or the salts thereof, wherein R?1, R2, R3¿, X, Y and Z are defined as in Claim 1 and (B) one or more herbicides selected from special herbicides from the following groups of compounds: (B1) herbicides which are selectively effective in some dicotyle cultures against monocotyle and dicotyle harmful plants, (B2) herbicides which are selectively effective in some dicotyle cultures and mainly against dicotyle harmful plants and (B3) herbicides which are selectively effective in some dicotyle cultures and mainly against monocotyle harmful plants.

Description

Beschreibungdescription
Herbizid-Kombination mit acylierten AminophenylsulfonylhamstoffenHerbicide combination with acylated aminophenylsulfonylureas
Die Erfindung liegt auf dem technischen Gebiet der Pflanzenschutzmittel, die gegen Schadpflanzen z.B. in Pflanzenkulturen eingesetzt werden können und als Wirkstoffe eine Kombination von mindestens zwei Herbiziden enthalten.The invention is in the technical field of crop protection agents which are used against harmful plants e.g. can be used in plant crops and contain a combination of at least two herbicides as active ingredients.
Aus der Druckschrift WO 95/29899 sind acylierte Aminophenylsulfonylharnstoffe und deren Salze sowie deren Verwendung als Herbizide und/oder Pflanzenwachstumsregulatoren bekannt. Unter Verbindungen dieser Strukturklasse sind von besonderem Interesse die Verbindungen der Formel (I) und deren Salze,From document WO 95/29899 acylated aminophenylsulfonylureas and their salts and their use as herbicides and / or plant growth regulators are known. Of compounds of this structural class, the compounds of the formula (I) and their salts are of particular interest,
worin wherein
R )11 Wasserstoff oder (C1-C4)Alkyl, vorzugsweise Methyl oder Ethyl, insbesondereR) 1 1 hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
Methyl, R2 Wasserstoff oder (C1-C4)Alkyl, vorzugsweise Methyl oder Ethyl, insbesondereMethyl, R 2 is hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
Methyl, R3 Wasserstoff, (CrC4)Alkyl, (CrC4)Alkoxy, (C2-C4)Alkenoxy, (C2-C4)Alkinoxy,Methyl, R 3 hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C 2 -C 4 ) alkenoxy, (C 2 -C 4 ) alkynoxy,
(C3-C6)Cycloalkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (C(C 3 -C 6 ) cycloalkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, cyano, (C
C4)Alkoxy und (C C4)Alkylsulfonyl substituiert ist, vorzugsweise Wasserstoff, Methyl, Trifiuormethyl, Ethyl, n-Propyl, Isopropyl,C 4 ) alkoxy and (CC 4 ) alkylsulfonyl is substituted, preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl,
Cyclopropyl, Methoxy oder Ethoxy, vorzugsweise Wasserstoff, Methyl oder Methoxy, insbesondere Wasserstoff, einer der Reste X und Y Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy und (CrC4)Alkylthio substituiert ist, und der andere der Reste X und Y (C1-C4)Alkyl, (C C4)Alkoxy oder (C C4)Alkylthio ist, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy und (Cr Cyclopropyl, methoxy or ethoxy, preferably hydrogen, methyl or Methoxy, in particular hydrogen, one of the radicals X and Y halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, each of the last three radicals being unsubstituted or by one or more radicals from the group consisting of halogen, (CC 4 ) alkoxy and (C r C 4 ) alkylthio, and the other of the radicals X and Y (C 1 -C 4 ) alkyl, (CC 4 ) alkoxy or (CC 4 ) Alkylthio, where each of the last three radicals is unsubstituted or by one or more radicals from the group halogen, (CC 4 ) alkoxy and (C r
C4)Alkylthio substituiert ist, insbesondere X und Y jeweils Methoxy, und Z CH oder N, insbesondere CH bedeuten.C 4 ) alkylthio is substituted, in particular X and Y are each methoxy, and Z is CH or N, in particular CH.
Die Wirksamkeit dieser Herbizide gegen Schadpfianzen in den Pflanzenkulturen liegt auf einem hohen Niveau, hängt jedoch im allgemeinen von der Aufwandmenge, der jeweiligen Zubereitungsform, den jeweils zu bekämpfenden Schadpflanzen oder dem Schadpflanzenspektrum, den Klima- und Bodenverhältnissen, etc. ab. Ein weiteres Kriterium ist die Dauer der Wirkung bzw. die Abbaugeschwindigkeit des Herbizids. Zu berücksichtigen sind gegebenenfalls auch Veränderungen in der Empfindlichkeit von Schadpflanzen, die bei längerer Anwendung der Herbzide oder geographisch begrenzt auftreten können. Wirkungsverluste bei einzelnen Schadpflanzen lassen sich nur bedingt durch höhere Aufwandmengen der Herbizide ausgleichen, z. B. weil damit häufig die Selektivität der Herbizide verschlechtert wird oder eine Wirkungsverbesserung auch bei höhere Aufwandmenge nicht eintritt. Teilweise kann die Selektivität in Kulturen durch Zusatz von Safenern verbessert werden. Generell besteht jedoch immer Bedarf für Methoden, die Herbizidwirkung mit geringerer Aufwandmenge an Wirkstoffen zu erreichen. Eine geringere Aufwandmenge reduziert nicht nur die für die Applikation erforderliche Menge eines Wirkstoffs, sondern reduziert in der Regel auch die Menge an nötigen Formulierungshilfsmittein. Beides verringert den wirtschaftlichen Aufwand und verbessert die ökologische Verträglichkeit der Herbizidbehandlung. Eine Möglichkeit zur Verbesserung des Anwendungsprofils eines Herbizids kann in der Kombination des Wirkstoffs mit einem oder mehreren anderen Wirkstoffen bestehen. Allerdings treten bei der kombinierten Anwendung mehrerer Wirkstoffe nicht selten Phänomene der physikalischen und biologischen Unverträglichkeit auf, z. B. mangelnde Stabilität in einer Coformulierung, Zersetzung eines Wirkstoffes bzw. Antagonismus der Wirkstoffe. Erwünscht dagegen sind Kombinationen von Wirkstoffen mit günstigem Wirkungsprofil, hoher Stabilität und möglichst synergistisch verstärkter Wirkung, welche eine Reduzierung der Aufwandmenge im Vergleich zur Einzelapplikation der zu kombinierenden Wirkstoffe erlaubt.The effectiveness of these herbicides against harmful plants in plant crops is at a high level, but generally depends on the application rate, the particular form of preparation, the harmful plants to be controlled or the range of harmful plants, the climate and soil conditions, etc. Another criterion is the duration of action or the rate of degradation of the herbicide. If necessary, changes in the sensitivity of harmful plants that may occur with extended use of the herbicides or geographically limited must also be taken into account. Loss of activity in individual harmful plants can only be compensated for to a limited extent by higher amounts of herbicides, for. B. because this often worsens the selectivity of the herbicides or does not result in an improvement in activity, even with a higher application rate. In some cases, the selectivity in cultures can be improved by adding safeners. In general, however, there is always a need for methods to achieve the herbicidal action with a lower application rate of active compounds. A lower application rate not only reduces the amount of an active ingredient required for the application, but generally also reduces the amount of formulation auxiliaries required. Both reduce the economic effort and improve the ecological compatibility of herbicide treatment. One way to improve the application profile of a herbicide is to combine the active ingredient with one or more other active ingredients. However, phenomena of physical and biological incompatibility often occur with the combined use of several active ingredients, e.g. B. lack of stability in a co-formulation, decomposition of an active ingredient or antagonism of the active ingredients. On the other hand, combinations of active ingredients with a favorable activity profile, high stability and, as far as possible, synergistically enhanced action are desired, which allow a reduction in the application rate compared to the individual application of the active ingredients to be combined.
Überraschenderweise wurde nun gefunden, daß Wirkstoffe aus der Gruppe der genannten Herbizide der Formel (I) oder deren Salzen in Kombination mit bestimmten strukturell verschiedenen Herbiziden in besonders günstiger Weise zusammenwirken, z.B. wenn sie in Pflanzenkulturen eingesetzt werden, die für die selektive Anwendung der Herbizide, gegebenenfalls unter Zusatz von Safeners, geeignet sind.Surprisingly, it has now been found that active compounds from the group of the herbicides of the formula (I) or their salts in combination with certain structurally different herbicides interact in a particularly advantageous manner, e.g. if they are used in plant crops which are suitable for the selective application of the herbicides, if appropriate with the addition of safeners.
Gegenstand der Erfindung sind somit Herbizid-Kombinationen mit einem wirksamen Gehalt an Komponenten (A) und (B), wobeiThe invention thus relates to herbicide combinations with an effective content of components (A) and (B), wherein
(A) ein oder mehrere Herbizide aus der Gruppe der Verbindungen der Formel (I) oder deren Salzen bedeutet,(A) one or more herbicides from the group of the compounds of the formula (I) or their salts,
worin wherein
R ) 1 Wasserstoff oder (C1-C4)Alkyl, vorzugsweise Methyl oder Ethyl, insbesondere Methyl, R2 Wasserstoff oder (C1-C4)Alkyl, vorzugsweise Methyl oder Ethyl, insbesondereR) 1 hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular methyl, R 2 is hydrogen or (C 1 -C 4 ) alkyl, preferably methyl or ethyl, in particular
Methyl, R3 Wasserstoff, (CrC4)Alkyl, (C C4)Alkoxy, (C2-C4)Alkenoxy, (C2-C4)Alkinoxy, (C3-C6)Cycloalkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (C C4)Alkoxy und (C C4)Alkylsulfonyl substituiert ist, vorzugsweise Wasserstoff, Methyl, Trifluormethyl, Ethyl, n-Propyl, Isopropyl, Cyclopropyl, Methoxy oder Ethoxy, vorzugsweise Wasserstoff, Methyl oder Methoxy, insbesondere Wasserstoff, einer der Reste X und Y Halogen, (C1-C4)Alkyl, (CrC4)Alkoxy, (CrC4)Alkylthio, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (CrC4)Alkoxy und (C1-C4)Alkylthio substituiert ist, und der andere der Reste X und Y (CrC4)Alkyl, (C C4)Alkoxy oder (CrC4)Alkylthio ist, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy und (C,- C4)Alkylthio substituiert ist, insbesondere X und Y jeweils Methoxy, und Z CH oder N, insbesondere CH bedeuten undMethyl, R 3 hydrogen, (C r C 4 ) alkyl, (CC 4 ) alkoxy, (C 2 -C 4 ) alkenoxy, (C 2 -C 4 ) alkynoxy, (C 3 -C 6 ) cycloalkyl, each of which 5 last-mentioned radicals unsubstituted or substituted by one or more radicals from the group halogen, cyano, (CC 4 ) alkoxy and (CC 4 ) alkylsulfonyl, preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy or Ethoxy, preferably hydrogen, methyl or methoxy, especially hydrogen, one of the radicals X and Y halogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, each of the latter three Radicals are unsubstituted or substituted by one or more radicals from the group halogen, (C r C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, and the other of the radicals X and Y (C r C 4 ) alkyl, (CC 4 ) Alkoxy or (C r C 4 ) alkylthio, where each of the last three radicals is unsubstituted or by one or more radicals from the group halogen, (CC 4 ) alkoxy and (C, - C 4 ) alkylthio is substituted, in particular X and Y are each methoxy, and Z is CH or N, in particular CH and
(B) bedeutet ein oder mehrere Herbizide aus der Gruppe der Verbindungen, bestehend aus (Angabe mit dem "common name" und der Referenzstelle aus "The Pesticide Manual" 11th Ed., British Crop Protection Council 1997, abgekürzt "PM")(B) means one or more herbicides from the group of the compounds consisting of (indication with the "common name" and the reference point from "The Pesticide Manual" 11th Ed., British Crop Protection Council 1997, abbreviated "PM")
(B1 ) selektiv in einigen dikotylen Kulturen gegen monokotyle und dikotyle Schadpflanzen wirksamen Herbiziden, ausgewählt aus der Gruppe bestehend aus:(B1) selectively herbicides active in some dicotyledon crops against monocotyledonous and dicotyledonous harmful plants, selected from the group consisting of:
(B1.1 ) Ethofumesate (PM, S. 484-486), d. h. Methansulfonsäure-(2- ethoxy-2,3 dihydro-3,3-dimethylbenzofuran-5-yl)-ester,(B1.1) Ethofumesate (PM, pp. 484-486), d. H. Methanesulfonic acid (2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl) ester,
(Aufwandmenge: 10 - 3000g AS/ha, vorzugsweise 20 - 1500g AS/ha; Aufwandmengenverhältnis A : B = 1 : 1000 - 12 : 1 , vorzugsweise 1 : 300 - 4 : 1 ); (B1.2) Chloridazon (PM, S.215-216), d. h.5-Amino-4-chlor-2-phenyl- pyridazin-3(2H)-on, (Aufwandmenge: 50 - 3000g AS/ha, vorzugsweise 80 - 2000g AS/ha; Aufwandmengenverhältnis A : B = 1 : 3000 -1 : 1, vorzugsweisel : 700 - 1 : 3);(Application rate: 10 - 3000g AS / ha, preferably 20 - 1500g AS / ha; application ratio A: B = 1: 1000 - 12: 1, preferably 1: 300 - 4: 1); (B1.2) Chloridazon (PM, p.215-216), ie 5-amino-4-chloro-2-phenyl-pyridazin-3 (2H) -one, (application rate: 50 - 3000 g ai / ha, preferably 80 - 2000g AS / ha; application rate ratio A: B = 1: 3000 -1: 1, preferably: 700 - 1: 3);
(B1.3) Triflusulfuron und dessen Ester, wie der Methylester, (PM, S. 1250-1252), d.h.2-[4-(Dimethylamino)-6-(2,2,2-trifluorethoxy)- 1,3,5-triazin-2-yl]-carbamoylsulfamoyl]-6-methyl-benzoesäure bzw. -methylester, (Aufwandmenge: 1 - 50g AS/ha, vorzugsweise 2 - 40g AS/ha; Aufwandmengenverhältnis A : B =(B1.3) triflusulfuron and its esters, such as the methyl ester, (PM, pp. 1250-1252), ie 2- [4- (dimethylamino) -6- (2,2,2-trifluoroethoxy) - 1,3, 5-triazin-2-yl] -carbamoylsulfamoyl] -6-methyl-benzoic acid or methyl ester, (application rate: 1 - 50g ai / ha, preferably 2 - 40g ai / ha; application rate ratio A: B =
1 : 50 - 1 : 2, vorzugsweise 1 : 15 - 1 : 3); (B1.4) Metamitron (PM, S.799-801), d.h.4-Amino-4,5-dihydro-3- methyl-6-phenyl-1,2,4-triazin-5-on, (Aufwandmenge: 50 -5000g AS/ha, vorzugsweise 80 - 4000g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 -1 :1 , vorzugsweise 1 : 1300 -1 :2) (B1.5) Metazachlor (PM, S.801-803), d. h.2-Chlor-N-(2,6- dimethylphenyl)-N-(1 H-pyrazol-1 -ylmethyl)-acetanilid, (Aufwandmenge: 100 - 3000 g AS/ha, vorzugsweise 200 - 2500 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 3000 -2: 1, vorzugsweise 1 : 800 -1 : 1); (B1.6) Napropamide (PM, S.866-868), d. h. (R,S)-N,N-Diethyl-2-(1- naphthyloxy)-propanamid, (Aufwandmenge: 200 - 3000 g AS/ha, vorzugsweise 300 - 2500 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 3000 -4: 1, vorzugsweise 1 : 800 - 2 : 1); (B1.7) Carbetamide (PM, S.184-185), d. h. (R)-Carbanilinsäure-I- (ethylcarbamoyl)-ethylester, (Aufwandmenge: 500 - 5000 g AS/ha, vorzugsweise 800 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 -10: 1, vorzugsweise 1 : 1300 -5: 1); (B1.8) Dimefuron (PM, S.403-404), d. h.3-[4-(5-tert.-Butyl-2,3-dihydro- 2-oxo-1, 3,4-oxadiazol-3-yl)-3-chlorphenyl]-N,N- dimethylhamstoff; (Aufwandmenge: 200 - 4000 g AS/ha, vorzugsweise 300 - 3000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 4000 -3 : 1 , vorzugsweise 1 : 1000-2 : 1);1:50 - 1: 2, preferably 1:15 - 1: 3); (B1.4) Metamitron (PM, p.799-801), ie 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one, (application rate: 50 -5000g AS / ha, preferably 80 - 4000g AS / ha; application ratio A: B = 1: 5000 -1: 1, preferably 1: 1300 -1: 2) (B1.5) metazachlor (PM, S.801-803 ), ie 2-chloro-N- (2,6-dimethylphenyl) -N- (1 H-pyrazol-1-ylmethyl) -acetanilide, (application rate: 100 - 3000 g ai / ha, preferably 200 - 2500 g ai / ha ; Application rate ratio A: B = 1: 3000 -2: 1, preferably 1: 800 -1: 1); (B1.6) Napropamide (PM, S.866-868), ie (R, S) -N, N-diethyl-2- (1-naphthyloxy) propanamide, (application rate: 200 - 3000 g AS / ha, preferably 300 - 2500 g AS / ha; application rate ratio A: B = 1: 3000 -4: 1, preferably 1: 800 - 2: 1); (B1.7) carbetamides (PM, pp. 184-185), ie (R) -carbanilinic acid I- (ethylcarbamoyl) ethyl ester, (application rate: 500-5000 g ai / ha, preferably 800-4000 g ai / ha ; Application rate ratio A: B = 1: 5000 -10: 1, preferably 1: 1300 -5: 1); (B1.8) Dimefuron (PM, p.403-404), ie 3- [4- (5-tert-butyl-2,3-dihydro-2-oxo-1, 3,4-oxadiazol-3-yl ) -3-chlorophenyl] -N, N-dimethyl urea; (Application rate: 200 - 4000 g ai / ha, preferably 300 - 3000 g ai / ha; application rate ratio A: B = 1: 4000 -3: 1, preferably 1: 1000-2: 1);
(B1.9) Dimethachlor (PM, S.406-407), 2-Chlor-N-(2,6-dimethylphenyl)- N-(2-methoxyethyl)-aceto-2',6'-xylilid, (Aufwandmenge: 30 - 4000 g AS/ha, vorzugsweise 200 - 3000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 4000 -2: 1, vorzugsweise 1 : 1000 - 1 : 1);(B1.9) Dimethachlor (PM, p.406-407), 2-chloro-N- (2,6-dimethylphenyl) - N- (2-methoxyethyl) -aceto-2 ', 6'-xylilide, (application rate : 30 - 4000 g ai / ha, preferably 200 - 3000 g ai / ha; application rate ratio A: B = 1: 4000 -2: 1, preferably 1: 1000 - 1: 1);
(B1.10)Norflurazon (PM, S.886-888), d. h.4-Chlor-5-(methylamino)-2- [3-(thfluormethyl)-phenyl]-3-(2H)-pyhdazinon (Aufwandmenge: 500 - 6000 g AS/ha, vorzugsweise 400 - 5000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 6000 -4: 1, vorzugsweise 1 : 2000 -3: 1);(B1.10) Norflurazon (PM, pp.886-888), d. h.4-chloro-5- (methylamino) -2- [3- (thfluoromethyl) phenyl] -3- (2H) -pyhdazinone (application rate: 500 - 6000 g ai / ha, preferably 400 - 5000 g ai / ha ; Application rate ratio A: B = 1: 6000 -4: 1, preferably 1: 2000 -3: 1);
(B1.11)Fluometuron (auch "Meturon", PM, S.578-579), d. h. N,N- Dimethyl-N'-[3-(trifluormethyl)-phenyl]-harnstoff (Aufwandmenge: 100 - 3000 g AS/ha, vorzugsweise 200 - 2500 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 3000 -2: 1, vorzugsweise 1 : 800 - 1 : 1 );(B1.11) Fluometuron (also "Meturon", PM, p.578-579), i.e. H. N, N-dimethyl-N '- [3- (trifluoromethyl) phenyl] urea (application rate: 100 - 3000 g ai / ha, preferably 200 - 2500 g ai / ha; application rate ratio A: B = 1: 3000 -2 : 1, preferably 1: 800-1: 1);
(B1.12)Methylarsonsäure der Formel CH3As(=O)(OH)2 und deren(B1.12) methylarsonic acid of the formula CH3As (= O) (OH) 2 and their
Salze wie DSMA = Dinatriumsalz oder MSMA = Mononatriumsalz von Methylarsonsäure (PM, S.821-823) (Aufwandmenge: 500 - 7000 g AS/ha, vorzugsweise 600 - 6000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 7000 -7: 1, vorzugsweise 1 : 2000 -5: 1); (B1.13)Diuron (PM, S.443-445), d. h. 3-(3,4-Dichlorphenyl)-1,1- dimethyl-harnstoff (Aufwandmenge 100 - 5000 g AS/ha, vorzugsweise 200 - 4000g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000-2 : 1 , vorzugsweise 1 : 1300-1 : 1), (B1.14)Prometryn (Promethyrin) (PM, S.1011-1013), d. h. N,N'-Bis(1- methylethyl)-6-methylthio)-2,4-diamino-1,3,5-triazin (Aufwandmenge: 50 - 5000 g AS/ha, vorzugsweise 80 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 -1 : 1, vorzugsweise 1 : 1300 - 1 : 2),Salts such as DSMA = disodium salt or MSMA = monosodium salt of methylarsonic acid (PM, S.821-823) (application rate: 500 - 7000 g AS / ha, preferably 600 - 6000 g AS / ha; application rate ratio A: B = 1: 7000 -7 : 1, preferably 1: 2000 -5: 1); (B1.13) Diuron (PM, p.443-445), ie 3- (3,4-dichlorophenyl) -1,1-dimethyl-urea (application rate 100 - 5000 g ai / ha, preferably 200 - 4000g ai / ha; application ratio A: B = 1: 5000-2: 1, preferably 1: 1300-1: 1), (B1.14) prometryn (promethyrin) (PM, S.1011-1013), ie N, N'- bis (1- methylethyl) -6-methylthio) -2,4-diamino-1,3,5-triazine (application rate: 50 - 5000 g ai / ha, preferably 80 - 4000 g ai / ha; application rate ratio A: B = 1: 5000 - 1: 1, preferably 1: 1300 - 1: 2),
(B1.15)Trifluralin (PM, S.1248-1250), d.h. , , -trifluoro-2,6-dinitro- N,N-dipropyl-p-toluol, (Aufwandmenge: 250 - 5000 g AS/ha, vorzugsweise 400 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000-1 : 1 , vorzugsweise 1 : 1200-4 : 1); (B1.16)Sulfentrazone (PM, S.1126-1127), d.h.2',4'-dichloro-5'-(4- difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1 ,2,4-triazol-1 - yl)methansulfonanilid, (Aufwandmenge: 50 - 2000 g AS/ha, vorzugsweise 70 - 1500 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 2000 -3:1, vorzugsweise 1 : 500 - 1 : 1 );(B1.15) trifluralin (PM, p.1248-1250), i.e. ,, -trifluoro-2,6-dinitro- N, N-dipropyl-p-toluene, (application rate: 250 - 5000 g ai / ha, preferably 400 - 4000 g ai / ha; application rate ratio A: B = 1: 5000- 1: 1, preferably 1: 1200-4: 1); (B1.16) Sulfentrazone (PM, S.1126-1127), ie 2 ', 4'-dichloro-5' - (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H- 1, 2,4-triazol-1 - yl) methanesulfonanilide, (application rate: 50 - 2000 g ai / ha, preferably 70 - 1500 g ai / ha; application rate ratio A: B = 1: 2000 -3: 1, preferably 1: 500-1: 1);
(B1.17)Ethalfluralin (PM, S.473-474), d.h. N-ethyl- , ,α-trifluoro-N-(2- methylallyl)-2,6-dinitro-p-toluol, (Aufwandmenge: 250 - 5000 g AS/ha, vorzugsweise 500 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 -2: 1, vorzugsweise 1 : 1300 -1 :5);(B1.17) Ethalfluralin (PM, p.473-474), i.e. N-ethyl-,, α-trifluoro-N- (2-methylallyl) -2,6-dinitro-p-toluene, (application rate: 250 - 5000 g ai / ha, preferably 500 - 4000 g ai / ha; application rate ratio A : B = 1: 5000 -2: 1, preferably 1: 1300 -1: 5);
(B1.18)Vernolate (PM, S.1264-1266), d.h. S-propyl dipropylthiocarbamat, (Aufwandmenge: 250 - 5000 g AS/ha, vorzugsweise 500 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 -2: 1, vorzugsweise 1 : 3000 -1 :5);(B1.18) Vernolate (PM, S.1264-1266), i.e. S-propyl dipropylthiocarbamate, (application rate: 250-5000 g ai / ha, preferably 500-4000 g ai / ha; application ratio A: B = 1: 5000-2: 1, preferably 1: 3000-1: 5);
(B1.19)Flumioxazin (PM, S.576-577), d.h. N-(7-fluoro-3,4-dihydro-3- oxo-4-prop-2-ynyl-2H-1 ,4-benzoxazin-6-yl)cyclohex-1-ene-1 ,2- dicarboxamid, (Aufwandmenge: 10 - 500 g AS/ha, vorzugsweise 20 - 400 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 500 - 12:1, vorzugsweise 1 : 300 -5:1);(B1.19) flumioxazin (PM, p.576-577), i.e. N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl) cyclohex-1-ene-1,2-dicarboxamide, ( Application rate: 10 - 500 g ai / ha, preferably 20 - 400 g ai / ha; ratio A: B = 1: 500 - 12: 1, preferably 1: 300 -5: 1);
(B2) selektiv in einigen dikotylen Kulturen überwiegend gegen dikotyle Schadpflanzen wirksamen Herbiziden, ausgewählt aus der Gruppe bestehend aus (B2.1 ) Desmedipham (PM, S. 349-350), d.h., N-[3-(B2) selectively in some dicotyledon crops, herbicides active predominantly against dicotyledonous harmful plants, selected from the group consisting of (B2.1) Desmedipham (PM, pp. 349-350), ie, N- [3-
(Ethoxycarbonylamino)phenyl]-carbaminsäure-phenyl-ester, (Aufwandmenge: 10 - 5000 g AS/ha, vorzugsweise 50 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 - 1 : 2, vorzugsweise 1 : 1300 - 1 : 3);(Ethoxycarbonylamino) phenyl] carbamic acid phenyl ester, (application rate: 10 - 5000 g ai / ha, preferably 50 - 4000 g ai / ha; application rate ratio A: B = 1: 5000 - 1: 2, preferably 1: 1300 - 1: 3);
(B2.2) Phenmedipham(PM, S. 948-949), d.h. N-[3-(B2.2) Phenmedipham (PM, pp. 948-949), i.e. N- [3-
(Methoxycarbonylamino)phenyl]-carbaminsäure-3- methylphenyl-ester, (Aufwandmenge: 10 - 5000 g AS/ha, vorzugsweise 50 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 - 1 : 2, vorzugsweise 1 : 1300 - 1 : 3);(Methoxycarbonylamino) phenyl] -carbamic acid 3-methylphenyl ester, (application rate: 10 - 5000 g ai / ha, preferably 50 - 4000 g ai / ha; application rate ratio A: B = 1: 5000 - 1: 2, preferably 1: 1300-1: 3);
(B2.3) Quinmerac (PM, S. 1080-1082), d.h., 7-Chlor-3-methyl-chinolin- 8-carbonsäure, (Aufwandmenge: 10 - 1000 g AS/ha, vorzugsweise 20 - 800 g AS/ha; Aufwandmengenverhäitnis A : B = 1 : 1000 - 1 : 4, vorzugsweise 1 : 260 - 1 : 5);(B2.3) Quinmerac (PM, pp. 1080-1082), ie 7-chloro-3-methyl-quinoline-8-carboxylic acid, (application rate: 10-1000 g ai / ha, preferably 20-800 g ai / ha; application rate ratio A: B = 1: 1000-1: 4, preferably 1: 260-1: 5);
(B2.4) Clopyralid (PM, S. 260-263), d. h. 3,6-Dichlorpyridin-2- carbonsäure und deren Salze, (Aufwandmenge: 20 - 1000 g AS/ha, vorzugsweise 30 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 1000 - 7 : 1 , vorzugsweise 1 : 260 - 3 : 1 );(B2.4) Clopyralid (PM, pp. 260-263), d. H. 3,6-dichloropyridine-2-carboxylic acid and its salts, (application rate: 20-1000 g ai / ha, preferably 30-800 g ai / ha; application ratio A: B = 1: 1000-7: 1, preferably 1: 260 - 3: 1);
(B2.5) Pyridate (PM, S. 1064-1066), d. h. O-(6-Chlor-3- phenylpyridazin-4-yl)-S-octyl-thiocarbonat, (Aufwandmenge: 100 - 5000 g AS/ha, vorzugsweise 200 - 3000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 - 1 ,5 : 1 , vorzugsweise 1 : 1000 - 1 : 1 );(B2.5) Pyridate (PM, pp. 1064-1066), d. H. O- (6-chloro-3-phenylpyridazin-4-yl) -S-octyl-thiocarbonate, (application rate: 100 - 5000 g ai / ha, preferably 200 - 3000 g ai / ha; application rate ratio A: B = 1: 5000 - 1, 5: 1, preferably 1: 1000 - 1: 1);
(B2.6) Ethametsulfuron-methyl (PM, S. 475-476), d. h. 2-{N-[N-(4- Ethoxy-6-methylamino-1 ,3,5-triazin-2-yl)-aminocarbonyl]- aminosulfonyl}-benzoesäuremethylester; (Aufwandmenge: 1 - 500 g AS/ha, vorzugweise 2 - 300 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 500 - 150 : 1 , vorzugsweise 1 : 100 - 90 : 1 );(B2.6) Ethametsulfuron-methyl (PM, pp. 475-476), d. H. 2- {N- [N- (4-Ethoxy-6-methylamino-1, 3,5-triazin-2-yl) aminocarbonyl] aminosulfonyl} benzoic acid methyl ester; (Application rate: 1 - 500 g AS / ha, preferably 2 - 300 g AS / ha; application ratio A: B = 1: 500 - 150: 1, preferably 1: 100 - 90: 1);
(B2.7) Pyrithiobac und dessen Salze, z. B. das Natriumsalz, (PM, S. 1073-1075), d. h. 2-Chlor-6-(4,6-dimethoxypyrimidin-2-ylthio)- benzoesäure-natriumsalz (Aufwandmenge: 5 - 300 g AS/ha, vorzugsweise 10 - 200 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 300 - 1 : 9, vorzugsweise 1 : 200 - 1 : 15);(B2.7) pyrithiobac and its salts, e.g. B. the sodium salt, (PM, S. 1073-1075), ie 2-chloro-6- (4,6-dimethoxypyrimidin-2-ylthio) - benzoic acid sodium salt (application rate: 5 - 300 g ai / ha, preferably 10 - 200 g ai / ha; application rate ratio A: B = 1: 300-1: 9, preferably 1: 200-1: 15);
(B2.8) Oxyfluorfen (PM, S. 919-921 ), d.h. 2-chloro-α,α,α-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether, (Aufwandmenge: 40 - 800 g AS/ha, vorzugsweise 60 - 600 g AS/ha;(B2.8) Oxyfluorfen (PM, pp. 919-921), i.e. 2-chloro-α, α, α-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether, (application rate: 40-800 g ai / ha, preferably 60-600 g ai / ha;
Aufwandmengenverhältnis A : B = 1 : 800 - 4 : 1 , vorzugsweise 1 : 200 - 1 : 1 );Application ratio A: B = 1: 800 - 4: 1, preferably 1: 200 - 1: 1);
(B2.9)Fomesafen (PM, S. 616-618), d.h. 5-(2-chloro-α,α,α-trifluoro-p- tolyloxyl)-N-methylsulfonyl-2-nitrobenzamid, (Aufwandmenge: 250 - 5000 g AS/ha, vorzugsweise 500 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 - 2 : 1 , vorzugsweise 1 : 1300 - 6 : 1 );(B2.9) Fomesafen (PM, pp. 616-618), i.e. 5- (2-chloro-α, α, α-trifluoro-p-tolyloxyl) -N-methylsulfonyl-2-nitrobenzamide, (application rate: 250 - 5000 g ai / ha, preferably 500 - 4000 g ai / ha; application rate ratio A : B = 1: 5000-2: 1, preferably 1: 1300-6: 1);
(B2.10)Flumiclorac (PM, S. 575-576), d.h. [2-chloro-5-(cyclohex-1-ene- 1 ,2-dicarboximido)-4-fluorophenoxy]essigsäure, und dessen Ester wie der Pentylester (Aufwandmenge: 10 - 400 g AS/ha, vorzugsweise 20 - 300 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 400 - 12 : 1 , vorzugsweise 1 : 100 - 5 : 1 );(B2.10) Flumiclorac (PM, pp. 575-576), i.e. [2-chloro-5- (cyclohex-1-ene-1, 2-dicarboximido) -4-fluorophenoxy] acetic acid, and its esters like the pentyl ester (application rate: 10 - 400 g ai / ha, preferably 20 - 300 g ai / ha; application rate ratio A: B = 1: 400-12: 1, preferably 1: 100-5: 1);
(B2.11 )2,4-DB (PM, S. 337-339), d.h. 4-(2,4- dichlorophenoxy)buttersäure, und dessen Ester und Salze (Aufwandmenge: 250 - 5000 g AS/ha, vorzugsweise 500 - 4000 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 5000 - 1 : 2, vorzugsweise 1 : 1300 - 1 : 5);(B2.11) 2,4-DB (PM, pp. 337-339), i.e. 4- (2,4-dichlorophenoxy) butyric acid, and its esters and salts (application rate: 250-5000 g ai / ha, preferably 500-4000 g ai / ha; application ratio A: B = 1: 5000-1: 2, preferably 1: 1300-1: 5);
(B2.12)Diclosulam (vgl. AG CHEM New Compound Review, Vol. 17, (1999) Seite 37, t azolopyrimidin-sulfonanilid-Herbizid)(B2.12) Diclosulam (see AG CHEM New Compound Review, Vol. 17, (1999) page 37, t azolopyrimidine sulfonanilide herbicide)
(Aufwandmenge: 5 - 150 g AS/ha, vorzugsweise 10-120 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 150 - 30 : 1 , vorzugsweise 1 : 40 - 9 : 1 ); (B2.13)Oxasulfuron (PM, S. 911-912), d.h. oxetan-3-yl 2-[(4,6- dimethylpyrimidin-2-yl)-carbamoylsulfamoyl]benzoat, (Aufwandmenge: 10-300 g AS/ha, vorzugsweise 20-200 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 100 - 3 : 1 , vorzugsweise 1 : 40 - 5 : 1 ); (Application rate: 5-150 g ai / ha, preferably 10-120 g ai / ha; application rate ratio A: B = 1: 150-30: 1, preferably 1:40 - 9: 1); (B2.13) Oxasulfuron (PM, pp. 911-912), ie oxetan-3-yl 2 - [(4,6-dimethylpyrimidin-2-yl) carbamoylsulfamoyl] benzoate, (application rate: 10-300 g AS / ha, preferably 20-200 g ai / ha; application ratio A: B = 1: 100 - 3: 1, preferably 1:40 - 5: 1);
(B3) selektiv in einigen dikotylen Kulturen überwiegend gegen monokotyle Schadpflanzen wirksamen Herbiziden ausgewählt aus der Gruppe bestehend aus(B3) selectively in some dicot crops predominantly herbicides active against monocotyledonous harmful plants selected from the group consisting of
(B3.1 ) Profluazol (AGROW, No. 338 October 15th, 1999, S. 26, PJB Publications Ltd. 1999, WO 97/15576), d.h. 1-chloro-N-[2- chloro-4-fluoro-5-[(6S, 7aR)-6-fluorotetrahydro-1 ,3-dioxo-1 H- pyrrolo[1 ,2-c]imidazol-2(3H)-yl]phenyl]-methansulfonamid, (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );(B3.1) profluazol (AGROW, No. 338 October 15 th, 1999, p 26, PJB Publications Ltd. 1999, WO 97/15576), or 1-chloro-N- [2- chloro-4-fluoro- 5 - [(6S, 7aR) -6-fluorotetrahydro-1, 3-dioxo-1 H-pyrrolo [1, 2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide, (application rate 5-1000 g AS / ha, preferably 5 - 800 g AS / ha; application ratio A: B = 1: 350 - 25: 1, preferably 1: 160 - 10: 1);
B3.2) Amicarbazone (AGROW, No. 338 October 15th, 1999, S. 26,B3.2) Amicarbazone (AGROW, No. 338 October 15 th , 1999, p. 26,
PJB Publications Ltd. 1999, DE 3839206), d.h. 4-amino-N-(1 ,1- dimethylethyl)-4,5-dihydro-3-(1 -methylethyl)-5-oxo-1 H-1 ,2,4- triazol-1-carboxamid), (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );PJB Publications Ltd. 1999, DE 3839206), i.e. 4-amino-N- (1,1-dimethylethyl) -4,5-dihydro-3- (1-methylethyl) -5-oxo-1 H-1, 2,4-triazole-1-carboxamide), (application rate 5 - 1000 g ai / ha, preferably 5 - 800 g ai / ha; application rate ratio A: B = 1: 350 - 25: 1, preferably 1: 160 - 10: 1);
B3.3) Pyriftalid (AGROW, No. 338 October 15 h, 1999, S. 26, PJBB3.3) Pyriftalid (AGROW, No. 338 October 15 h , 1999, p. 26, PJB
Publications Ltd. 1999, WO 91/05781 ), d.h. 7-[(4,6-dimethoxy-2- pyhmidinyl)thio]-3-methyl-1 (3H)-isobenzofuranon, (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );Publications Ltd. 1999, WO 91/05781), ie 7 - [(4,6-dimethoxy-2-pyhmidinyl) thio] -3-methyl-1 (3H) -isobenzofuranone, (application rate 5-1000 g ai / ha, preferably 5- 800 g AS / ha; application rate ratio A: B = 1: 350 - 25: 1, preferably 1: 160-10: 1);
B3.4) Trifloxysulfuron und dessen Salze, z.B. das Natriumsalz,B3.4) trifloxysulfuron and its salts, e.g. the sodium salt,
(AGROW, No. 338 October 15th, 1999, S. 26, PJB Publications Ltd. 1999, WO 92/16522), d.h. N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2- pyridinsulfonamid, (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );(AGROW, No. 338 October 15 th, 1999, p 26, PJB Publications Ltd. 1999, WO 92/16522), that N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3 - (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide, (application rate 5 - 1000 g ai / ha, preferably 5 - 800 g ai / ha; application rate ratio A: B = 1: 350 - 25: 1, preferably 1: 160-10: 1);
B3.5) Epocholeone (AGROW, No. 338 October 15,h, 1999, S. 26, PJB Publications Ltd. 1999, WO 94/28011 ), d.h. 1-[(1S)-1-[(2R, 3R)- 3-[(1 S)-1 -ethyl-2-methylpropyl]oxiranyl]ethyl]hexadeca-hydro- 10a,12a-dimethyl-8,9-bis(1-oxopropoxy)-(1 R, 3aS, 3bS, 6aS, 8S, 9R, 10aR, 10bS, 12aS)-6H-Benz[c]indeno[5,4-e]oxepin-6- one, (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );B3.5) Epocholeone (AGROW, No. 338 October 15 , h , 1999, p. 26, PJB Publications Ltd. 1999, WO 94/28011), ie 1 - [(1S) -1 - [(2R, 3R) - 3 - [(1 S) -1-ethyl-2-methylpropyl] oxiranyl] ethyl] hexadeca-hydro-10a, 12a-dimethyl-8,9-bis (1-oxopropoxy) - (1 R, 3aS, 3bS, 6aS, 8S, 9R, 10aR, 10bS, 12aS) -6H-Benz [c] indeno [5,4-e] oxepin-6- one, (application rate 5 - 1000 g AS / ha, preferably 5 - 800 g AS / ha; application rate ratio A: B = 1: 350-25: 1, preferably 1: 160-10: 1);
B3.6) Tepraloxydim (DE 4222261 ), d.h. 2-[1-[[[(2E)-3-chloro-2- propenyl]oxy]imino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4- yl)-2-cyclohexen-1-on, (Aufwandmenge 5 - 1000 g AS/ha, vorzugsweise 5 - 800 g AS/ha; Aufwandmengenverhältnis A : B = 1 : 350 - 25 : 1 , vorzugsweise 1 : 160 - 10 : 1 );B3.6) Tepraloxydim (DE 4222261), i.e. 2- [1 - [[[(2E) -3-chloro-2-propenyl] oxy] imino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1 -on, (application rate 5-1000 g ai / ha, preferably 5-800 g ai / ha; application ratio A: B = 1: 350-25: 1, preferably 1: 160-10: 1);
Die erfindungsgemäßen Herbizid-Kombinationen weisen einen herbizid wirksamen Gehalt an Komponenten A und B auf und können weitere Komponenten enthalten, z. B. agrochemische Wirkstoffe anderer Art und/oder im Pflanzenschutz übliche Zusatzstoffe und/oder Formulierungshilfsmittel, oder zusammen mit diesen eingesetzt werden.The herbicide combinations according to the invention have a herbicidally active content of components A and B and can contain further components, for. B. agrochemical active substances of another type and / or additives and / or formulation auxiliaries customary in crop protection, or used together with these.
Die erfindungsgemäßen Herbizid-Kombinationen weisen synergistische Wirkungen auf. Die synergistischen Wirkungen werden bei gemeinsamer Ausbringung der Wirkstoffe (A) und (B) beobachtet, können jedoch häufig auch bei zeitlich versetzter Anwendung (Splitting) festgestellt werden. Möglich ist auch die Anwendung der einzelnen Herbizide oder der Herbizid-Kombinationen in mehreren Portionen (Sequenzanwendung), z. B. nach Anwendungen im Vorauflauf, gefolgt von Nachauflauf-Applikationen oder nach frühen Nachauflaufanwendungen, gefolgt von Applikationen im mittleren oder späten Nachauflauf. Bevorzugt ist dabei die gemeinsame oder die zeitnahe Anwendung der Wirkstoffe der erfindungsgemäßen Herbizid-Kombination.The herbicide combinations according to the invention have synergistic effects. The synergistic effects are observed when the active ingredients (A) and (B) are applied together, but can often also occur with a time delay Application (splitting) can be determined. It is also possible to use the individual herbicides or the herbicide combinations in several portions (sequence application), for. B. after pre-emergence applications, followed by post-emergence applications, or after early post-emergence applications, followed by applications in the middle or late post-emergence. Preferred is the simultaneous or prompt application of the active compounds of the herbicide combination according to the invention.
Die synergistischen Effekte erlauben eine Reduktion der Aufwandmengen der Einzelwirkstoffe, eine höhere Wirkungsstärke bei gleicher Aufwandmenge, die Kontrolle bislang nicht erfasster Arten (Lücken), eine Ausdehnung des Anwendungszeitraums und/oder eine Reduzierung der Anzahl notwendiger Einzelanwendungen und - als Resultat für den Anwender - ökonomisch und ökologisch vorteilhaftere Unkrautbekämpfungssysteme.The synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency with the same application rate, the control of previously unrecognized types (gaps), an extension of the application period and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and more environmentally friendly weed control systems.
Beispielsweise werden durch die erfindungsgemäßen Kombinationen aus (A)+(B) synergistische Wirkungssteigerungen möglich, die weit und in unerwarteter Weise über die Wirkungen hinausgehen, die mit den Einzelwirkstoffen (A) und (B) erreicht werden.For example, the combinations of (A) + (B) according to the invention enable synergistic increases in activity which go far and unexpectedly beyond the effects which are achieved with the individual active compounds (A) and (B).
Die herbiziden Kombinationspartner aus der Gruppe (B1 ) wirken gegen mono- und dikotyle Schadpflanzen. Die herbiziden Kombinationspartner aus der Gruppe (B2) wirken überwiegend gegen dikotyle Schadpflanzen, können zum Teil aber auch gegen monokolyte Schadpflanzen wirksam sein. Die herbiziden Kombinationspartner aus der Gruppe (B3) wirken überwiegend gegen monokotyle Schadpflanzen, können zum Teil aber auch gegen dikotyle Schadpflanzen wirksam sein.The herbicidal combination partners from group (B1) act against mono- and dicotyledonous harmful plants. The herbicidal combination partners from group (B2) mainly act against dicotyledonous harmful plants, but can also be effective in some cases against monocolyte harmful plants. The herbicidal combination partners from group (B3) mainly act against monocotyledonous harmful plants, but in some cases they can also be effective against dicotyledonous harmful plants.
Die genannte Formel (I) umfaßt alle Stereoisomeren und deren Gemische, insbesondere auch racemische Gemische, und - soweit Enantiomere möglich sind - das jeweils biologisch wirksame Enantiomere. Verbindungen der Formel (I) und ihre Herstellung sind z.B. beschrieben in WO 95/29899. Beispiele für Wirkstoffe der Formel (I) sind Verbindungen der Formel (A1) und deren SalzeThe formula (I) mentioned comprises all stereoisomers and their mixtures, in particular also racemic mixtures, and - insofar as enantiomers are possible - the biologically active enantiomer in each case. Compounds of formula (I) and their Production are described, for example, in WO 95/29899. Examples of active substances of the formula (I) are compounds of the formula (A1) and their salts
worin R3 definiert ist wie in Formel (I) und Me = Methyl ist, vorzugsweise die Verbindungen (A1.1 ) bis (A1.6)wherein R 3 is defined as in formula (I) and Me = methyl, preferably the compounds (A1.1) to (A1.6)
(A1.1 ) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(formylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =Wasserstoff, und dessen Salze, d.h. Foramsulfuron (AGROW No. 338, October 15,h 1999, Seite 26, PJB Publications Ltd. 1999);(A1.1) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (formylamino) benzenesulfonamide, ie formula (A1) with R 3 = Hydrogen, and its salts, ie foramsulfuron (AGROW No. 338, October 15 , 1999, page 26, PJB Publications Ltd. 1999);
(A1.2) N-[N-(4,6-Dimethoxypyhmidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(acetylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =Methyl, und dessen Salze;(A1.2) N- [N- (4,6-Dimethoxypyhmidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (acetylamino) benzenesulfonamide, ie formula (A1) with R 3 = Methyl, and its salts;
(A1.3) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(propionylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =Ethyl, und dessen Salze;(A1.3) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (propionylamino) benzenesulfonamide, ie formula (A1) with R 3 = Ethyl, and its salts;
(A1.4) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(isopropylcarbonylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =lsopropyl, und dessen Salze;(A1.4) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (isopropylcarbonylamino) benzenesulfonamide, ie formula (A1) with R 3 = isopropyl, and its salts;
(A1.5) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(methoxycarbonylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =Methoxy, und dessen Salze;(A1.5) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (methoxycarbonylamino) benzenesulfonamide, ie formula (A1) with R 3 = Methoxy, and its salts;
(A1.6) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(ethoxycarbonylamino)-benzolsulfonamid, d.h. Formel (A1 ) mit R3 =Ethoxy, und dessen Salze;(A1.6) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (dimethyl- aminocarbonyl) -5- (ethoxycarbonylamino) benzenesulfonamide, ie formula (A1) with R 3 = ethoxy, and its salts;
Weitere Beispiele für Wirkstoffe der Formel (I) sind Verbindungen der Formel (A2) und deren SalzeFurther examples of active substances of the formula (I) are compounds of the formula (A2) and their salts
worin R3 definiert ist wie in Formel (I) und Me = Methyl und Et = Ethyl bedeuten, vorzugsweise die Verbindungen (A2.1 ) bis (A2.6) wherein R 3 is defined as in formula (I) and Me = methyl and Et = ethyl, preferably the compounds (A2.1) to (A2.6)
(A2.1 ) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(diethyl-aminocarbonyl)-(A2.1) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (diethyl aminocarbonyl) -
5-(formylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =Wasserstoff, und dessen Salze; (A2.2) N-[N-(4,6-Dimethoxypyhmidin-2-yl)-aminocarbonyl]-2-(diethyl-aminocarbonyl)-5- (formylamino) benzenesulfonamide, ie formula (A2) with R 3 = hydrogen, and its salts; (A2.2) N- [N- (4,6-Dimethoxypyhmidin-2-yl) aminocarbonyl] -2- (diethyl aminocarbonyl) -
5-(acetylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =Methyl, und dessen Salze; (A2.3) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(propionylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =Ethyl, und dessen Salze; (A2.4) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(isopropylcarbonylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =lsopropyl, und dessen Salze; (A2.5) N-[N-(4,6-Dimethoxypyhmidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(methoxycarbonylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =Methoxy, und dessen Salze; (A2.6) N-[N-(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(ethoxycarbonylamino)-benzolsulfonamid, d.h. Formel (A2) mit R3 =Ethoxy, und dessen Salze;5- (acetylamino) -benzenesulfonamide, ie formula (A2) with R 3 = methyl, and its salts; (A2.3) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (propionylamino) benzenesulfonamide, ie formula (A2) with R 3 = Ethyl, and its salts; (A2.4) N- [N- (4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (isopropylcarbonylamino) benzenesulfonamide, ie formula (A2) with R 3 = isopropyl, and its salts; (A2.5) N- [N- (4,6-Dimethoxypyhmidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (methoxycarbonylamino) benzenesulfonamide, ie formula (A2) with R 3 = Methoxy, and its salts; (A2.6) N- [N- (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (ethoxycarbonylamino) benzenesulfonamide, ie formula (A2) with R 3 = ethoxy, and its salts;
Weitere Beispiele für Wirkstoffe der Formel (I) sind Verbindungen der Formel (A3) und deren SalzeFurther examples of active substances of the formula (I) are compounds of the formula (A3) and their salts
worin R1, R2 und R3wie in Formel (I) definiert sind und Me = Methyl bedeutet undwherein R 1 , R 2 and R 3 are as defined in formula (I) and Me = methyl and
R4 = Methoxy, Chlor oder Methyl ist, vorzugsweise die Verbindungen (A3.1 ) bis (A3.6)R 4 = methoxy, chlorine or methyl, preferably the compounds (A3.1) to (A3.6)
(A3.1 ) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(formylamino)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Wasserstoff und R1 = R2= Methyl, und dessen Salze;(A3.1) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (formylamino) benzenesulfonamide, ie formula (A3) with R 3 = hydrogen and R 1 = R 2 = methyl, and its salts;
(A3.2) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(acetylamino)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Methyl und R1 = R2= Methyl, und dessen Salze;(A3.2) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (acetylamino) benzenesulfonamide, ie formula (A3) with R 3 = methyl and R 1 = R 2 = methyl, and its salts;
(A3.3) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(dimethyl- aminocarbonyl)-5-(methoxycarbonyl)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Methoxy und R1 = R2= Methyl, und dessen Salze;(A3.3) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (dimethylaminocarbonyl) -5- (methoxycarbonyl) benzenesulfonamide, ie formula (A3) with R 3 = methoxy and R 1 = R 2 = methyl, and its salts;
(A3.4) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(formylamino)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Wasserstoff und R1 = R2= Ethyl, und dessen Salze;(A3.4) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (formylamino) benzenesulfonamide, ie formula (A3) with R 3 = hydrogen and R 1 = R 2 = ethyl, and its salts;
(A3.4) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(acetylamino)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Methyl und R1 = R2= Ethyl, und dessen Salze; (A3.5) N-[N-(4-Methoxy-6-methyl-pyrimidin-2-yl)-aminocarbonyl]-2-(diethyl- aminocarbonyl)-5-(methoxycarbonyl)-benzolsulfonamid, d.h. Formel (A3) mit R3 =Methoxy und R1 = R2= Ethyl, und dessen Salze.(A3.4) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (diethyl- aminocarbonyl) -5- (acetylamino) -benzenesulfonamide, ie formula (A3) with R 3 = methyl and R 1 = R 2 = ethyl, and its salts; (A3.5) N- [N- (4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl] -2- (diethylaminocarbonyl) -5- (methoxycarbonyl) benzenesulfonamide, ie formula (A3) with R 3 = methoxy and R 1 = R 2 = ethyl, and its salts.
Die genannten Herbizide der Formel (I) und deren Salze hemmen das Enzym Acetolactatsynthase (ALS) und damit die Proteinsynthese in Pflanzen. Die Aufwandmenge der Herbizide der Formel (I) kann in einem weiten Bereich variieren, beispielsweise zwischen 0,001 und 0,5 kg AS/ha (AS/ha bedeutet „Aktivsubstanz pro Hektar" = bezogen auf 100%igen Wirkstoff). Bei Anwendungen mit Aufwandmengen von 0,01 bis 0,1 kg AS/ha der Herbizide der Formel (I), vorzugsweise der Formeln (A1 ), (A2) oder (A3), insbesondere (A1 ), wird im Vor- und Nachauflaufverfahren ein relativ breites Spektrum an annuellen und perennierenden Unkräutern, Ungräsem sowie Cyperaceen bekämpft. Bei den erfindungsgemäßen Kombinationen liegen die Aufwandmengen in der Regel niedriger, z. B. im Bereich von 0,5 bis 120 g AS/ha, vorzugsweise 2 bis 80 g AS/ha. Die Wirkstoffe können in der Regel als wasserlösliches Spritzpulver (WP), wasserdispergierbares Granulat (WDG), wasseremulgierbares Granulat (WEG), Suspoemulsion (SE) oder Ölsuspensionskonzentrat (SC) formuliert werden.The herbicides of formula (I) and their salts inhibit the enzyme acetolactate synthase (ALS) and thus the protein synthesis in plants. The application rate of the herbicides of the formula (I) can vary within a wide range, for example between 0.001 and 0.5 kg of AS / ha (AS / ha means “active substance per hectare” = based on 100% active ingredient). For applications with application rates From 0.01 to 0.1 kg of AS / ha of the herbicides of the formula (I), preferably of the formulas (A1), (A2) or (A3), in particular (A1), a relatively broad spectrum is obtained in the pre- and post-emergence process in the combinations according to the invention, the application rates are generally lower, for example in the range from 0.5 to 120 g ai / ha, preferably 2 to 80 g ai / ha Active ingredients can usually be formulated as water-soluble wettable powder (WP), water-dispersible granulate (WDG), water-emulsifiable granulate (WEG), suspoemulsion (SE) or oil suspension concentrate (SC).
Die im allgemeinen verwendeten Aufwandmengenverhältnisse A : B sind vorstehend angegeben und bezeichnen das Gewichtsverhältnis der beiden Komponenten A und B zueinander.The application rate ratios A: B used in general are given above and denote the weight ratio of the two components A and B to one another.
Zur Anwendung der Wirkstoffe der Formel (I) oder deren Salzen in Pflanzenkulturen kann es je nach Pflanzenkultur zweckmäßig sein, ab bestimmter Aufwandmengen einen Safener zu applizieren, um Schäden an der Kulturpflanze zu reduzieren oder zu vermeiden. Beispiele für geeignete Safener sind solche, die in Kombination mit Sulfonylharnstoff-Herbiziden, vorzugsweise, Phenylsulfonylharnstoffen Safenerwirkung entfalten. Geeignete Safener sind aus WO-A-96/14747 und der dort zitierten Literatur bekannt.To use the active compounds of the formula (I) or their salts in plant crops, depending on the plant culture, it may be expedient to apply a safener from certain application rates in order to reduce or avoid damage to the crop. Examples of suitable safeners are those which, in combination with sulfonylurea herbicides, preferably phenylsulfonylureas Develop safener effect. Suitable safeners are known from WO-A-96/14747 and the literature cited therein.
Folgende Gruppen von Verbindungen sind beispielsweise als Safener für die oben erwähnten herbiziden Wirkstoffe (A) geeignet:The following groups of compounds are suitable, for example, as safeners for the herbicidal active compounds (A) mentioned above:
a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1 ), vorzugsweise Verbindungen wiea) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid (S1) type, preferably compounds such as
1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3- carbonsäureethylester (S1-1 , Mefenpyr-diethyl), und verwandte Verbindungen, wie sie in der WO 91/07874 beschrieben sind, b) Derivate der Dichlorphenylpyrazolcarbonsäure, vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1-2), 1-(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1-3), 1-(2,4-Dichlorphenyl)-5-(1 ,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1 -4), 1 -(2,4-Dichlorphenyl)-5-phenyl-pyrazol-3-carbonsäureethylester (S1-5) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind. c) Verbindungen vom Typ der Triazolcarbonsäuren (S1 ), vorzugsweise Verbindungen wie Fenchlorazol, d.h.1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1, mefenpyr-diethyl), and related compounds, as described in WO 91/07874 b) Derivatives of dichlorophenylpyrazole carboxylic acid, preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5-isopropyl- ethyl pyrazole-3-carboxylate (S1-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) ethyl pyrazole-3-carboxylate (S1 -4), 1 - (2, 4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S1-5) and related compounds as described in EP-A-333 131 and EP-A-269 806. c) Compounds of the triazole carboxylic acid (S1) type, preferably compounds such as fenchlorazole, i.e.
1 -(2,4-Dichlorphenyl)-5-trichlormethyl-(1 H)-1 ,2,4-triazol-3- carbonsäureethylester (S1-6), und verwandte Verbindungen (siehe EP-A-174 562 und EP-A-346 620); d) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazoiin-3-carbonsäureethylester (S1-7) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1-8) und verwandte Verbindungen, wie sie in WO 91/08202 beschrieben sind, bzw. der 5,5-Diphenyl-2-isoxazoiin-carbonsäureethylester (S1-9, Isoxadifen-ethyl) oder -n-propylester (S1-10) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3- carbonsäureethylester (S1-11 ), wie sie in der Patentanmeldung (WO-A-95/07897) beschrieben sind. e) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2), vorzugsweise1 - (2,4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S1-6), and related compounds (see EP-A-174 562 and EP- A-346 620); d) Compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds such as 5- (2,4-dichlorobenzyl) -2-isoxazoiin-3-carboxylic acid ethyl ester (S1-7) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) and related compounds, as described in WO 91/08202, or 5.5 -Diphenyl-2-isoxazoiin-carboxylic acid ethyl ester (S1-9, isoxadifen-ethyl) or -n-propyl ester (S1-10) or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1 -11) as described in the patent application (WO-A-95/07897). e) Compounds of the 8-quinolinoxyacetic acid (S2) type, preferably
(5-Chlor-8-chinol inoxy)-essigsäure-(1 -methyl-hex-1 -yl)-ester (S2-1 ),(5-chloro-8-quinol inoxy) acetic acid (1-methyl-hex-1-yl) ester (S2-1),
(5-Chlor-8-chinol iinoxy)-essigsäure-(1 ,3-dimethyl-but-1-yl)-ester (S2-2),(5-chloro-8-quinol iinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2),
(5-Chlor-8-chinol inoxy)-essigsäure-4-allyl-oxy-butylester (S2-3),(5-chloro-8-quinol inoxy) -acetic acid-4-allyl-oxy-butyl ester (S2-3),
(5-Chlor-8-chinol iinoxy)-essigsäure-1 -allyioxy-prop-2-ylester (S2-4),(5-chloro-8-quinol iinoxy) -acetic acid-1-allyioxy-prop-2-yl ester (S2-4),
(5-Chlor-8-chinol inoxy)-essigsäureethylester (S2-5),(5-chloro-8-quinol inoxy) ethyl acetate (S2-5),
(5-Chlor-8-chinol inoxy)-essigsäuremethylester (S2-6),(5-chloro-8-quinol inoxy) -acetic acid methyl ester (S2-6),
(5-Chlor-8-chinol inoxy)-essigsäureallylester (S2-7),(5-chloro-8-quinol inoxy) -acetic acid allyl ester (S2-7),
(5-Chlor-8-chinol inoxy)-essigsäure-2-(2-propyliden-iminoxy)-1- ethylester (S2-8),(5-chloro-8-quinol inoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)-essigsäure-2-oxo-prop-1 -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und(5-Chloro-8-quinolinoxy) -acetic acid-2-oxo-prop-1-ethyl ester (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and
EP-A-191 736 oder EP-A-0 492 366 beschrieben sind. f) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)-malonsäure, vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)-malonsäure- diethylester, (5-Chlor-8-chinolinoxy)-malonsäurediallylester, (5-Chlor-8-chinolinoxy)-malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. g) Wirkstoffe vom Typ der Phenoxyessig- bzw. -propionsäurederivate bzw. der aromatischen Carbonsäuren, wie z.B. 2,4-Dichlorphenoxyessigsäure(ester) (2,4-D), 4-Chlor-2-methyl-phenoxy-propionester (Mecoprop), MCPA oder 3,6-Dichlor-2-methoxy-benzoesäure(ester) (Dicamba).EP-A-191 736 or EP-A-0 492 366. f) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid, preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5- Chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. g) active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type, e.g. 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop), MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (dicamba) ,
Für Wirkstoffe der Gruppe (B) sind die obengenannten Safener vielfach ebenfalls geeignet. Darüber hinaus eignen sich folgende Safener für die erfindungsgemäßenThe above-mentioned safeners are also often suitable for active ingredients of group (B). In addition, the following safeners are suitable for the inventive
Herbizid-Kombinationen: h) Wirkstoffe vom Typ der Pyrimidine, wie „Fenclorim" (PM, S. 512-511 ) (= 4,6-Herbicide combinations: h) active substances of the pyrimidines type, such as “Fenclorim” (PM, pp. 512-511) (= 4.6-
Dichlor-2-phenylpyrimidin), i) Wirkstoffe vom Typ der Dichloracetamide, die häufig als VorauflaufsafenerDichloro-2-phenylpyrimidine), i) Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z.B.(soil-safe safeners), such as
„Dichlormid" (PM, S. 363-364) (= N,N-Diallyl-2,2-dichloracetamid), AR-29148" (= 3-Dichloracetyl-2,2,5-trimethyl-1 ,3-oxazolidon von der Firma"Dichlormid" (PM, pp. 363-364) (= N, N-diallyl-2,2-dichloroacetamide), AR-29148 "(= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidone from the company
Stauffer),Stauffer)
„Benoxacor" (PM, s. 102-103) (= 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1 ,4- benzoxazin)."Benoxacor" (PM, see 102-103) (= 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine).
APPG-1292" (= N-Allyl-N[(1 ,3-dioxolan-2-yl)-methyl]dichloracetamid von derAPPG-1292 "(= N-allyl-N [(1,3-dioxolan-2-yl) methyl] dichloroacetamide from the
Firma PPG Industries),PPG Industries),
ADK-24" (= N-Allyl-N-[(allylaminocarbonyl)-methyl]-dichloracetamid von derADK-24 "(= N-allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide from the
Firma Sagro-Chem),Sagro-Chem),
AAD-67" oder AMON 4660" (= 3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan von der Firma Nitrokemia bzw. Monsanto),AAD-67 "or AMON 4660" (= 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane from Nitrokemia or Monsanto),
„Dicionon" oder ABAS 145138" oder ALAB145138" (= (= 3-Dichloracetyl-2,5,5- trimethyl-1 ,3-diazabiclyco[4.3.0]nonan von der Firma BASF) und"Dicionon" or ABAS 145138 "or ALAB145138" (= (= 3-dichloroacetyl-2,5,5-trimethyl-1, 3-diazabiclyco [4.3.0] nonane from BASF) and
„Furilazol" oder AMON 13900" (siehe PM, 637-638) (= (RS)-3-Dichloracetyl-5-"Furilazole" or AMON 13900 "(see PM, 637-638) (= (RS) -3-dichloroacetyl-5-
(2-furyl)-2,2-dimethyloxazolidon) j) Wirkstoffe vom Typ der Dichloracetonderivate, wie z.B.(2-furyl) -2,2-dimethyloxazolidone) j) active substances of the dichloroacetone derivative type, e.g.
AMG 191" (CAS-Reg. Nr. 96420-72-3) (= 2-Dichlormethyl-2-methyl-1 ,3- dioxolan von der Firma Nitrokemia), k) Wirkstoffe vom Typ der Oxyimino-Verbindungen, die als Saatbeizmittel bekannt sind, wie z.B.AMG 191 "(CAS Reg. No. 96420-72-3) (= 2-dichloromethyl-2-methyl-1,3-dioxolane from the company Nitrokemia), k) active substances of the oxyimino compound type, which are used as seed dressings are known, such as
„Oxabetrinil" (PM, S. 902-903) (= (Z)-1 ,3-Dioxolan-2- ylmethoxyimino(phenyl)acetonithl), das als Saatbeiz-Safener gegen Schäden von Metolachlor bekannt ist,"Oxabetrinil" (PM, pp. 902-903) (= (Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonithl), which is known as a seed dressing safener against damage to metolachlor,
„Fluxofenim" (PM, S. 613-614) (= 1-(4-Chlorphenyl)-2,2,2-trifluor-1-ethanon-"Fluxofenim" (PM, pp. 613-614) (= 1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-
O-(1 ,3-dioxolan-2-ylmethyl)-oxim, das als Saatbeiz-Safener gegen Schäden von Metolachlor bekannt ist, undO- (1, 3-dioxolan-2-ylmethyl) oxime, which is known as a seed dressing safener against damage to metolachlor, and
„Cyometrinil" oder A-CGA-43089" (PM, S. 1304) (= (Z)-Cyanomethoxyimino"Cyometrinil" or A-CGA-43089 "(PM, p. 1304) (= (Z) -cyanomethoxyimino
(phenyl)acetonitril), das als Saatbeiz-Safener gegen Schäden von(phenyl) acetonitrile), which acts as a seed dressing safener against damage from
Metolachlor bekannt ist, I) Wirkstoffe vom Typ der Thiazolcarbonsäureester, die als Saatbeizmittel bekannt sind, wie z.B.Metolachlor is known, I) active substances of the thiazole carboxylic acid ester type, which are known as seed dressings, such as
„Flurazol" (PM, S. 590-591 ) (= 2-Chlor-4-trifluormethyl-1 ,3-thiazol-5- carbonsäurebenzylester), das als Saatbeiz-Safener gegen Schäden von"Flurazole" (PM, pp. 590-591) (= 2-chloro-4-trifluoromethyl-1, 3-thiazole-5- carboxylic acid benzyl ester), which acts as a seed dressing safener against damage from
Alachlor und Metolachlor bekannt ist, m) Wirkstoffe vom Typ der Napthalindicarbonsäuredehvate, die alsAlachlor and Metolachlor is known, m) active substances of the type of Napthalindicarbonsäuredehvate, which
Saatbeizmittel bekannt sind, wie z.B.Seed dressings are known, e.g.
„Naphthalic anhydrid" (PM, S. 1342) (= 1 ,8-"Naphthalic anhydride" (PM, p. 1342) (= 1, 8-
Naphthalindicarbonsäureanhydrid), das als Saatbeiz-Safener für Mais gegenNaphthalenedicarboxylic anhydride), which acts as a seed dressing safener against corn
Schäden von Thiocarbamatherbiziden bekannt ist, n) Wirkstoffe vom Typ Chromanessigsäuredehvatre, wie z.B.Damage of thiocarbamate herbicides is known, n) active compounds of the chromanacetic acid dehvatre type, such as e.g.
ACL 304415" (CAS-Reg. Nr. 31541-57-8) (= 2-84-Carboxy-chroman-4-yl)- essigsäure von der Firma American Cyanamid), o) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auchACL 304415 "(CAS Reg. No. 31541-57-8) (= 2-84-carboxy-chroman-4-yl) - acetic acid from American Cyanamid), o) active ingredients which, in addition to a herbicidal action against harmful plants also
Safenerwirkung an Kulturpflanzen aufweisen, wie z.B.Have safener action on crops, e.g.
„Dimepiperate" oder AMY-93" (PM, S. 404-405) (= Piperidin-1- thiocarbonsäure-S-1 -methyl-1 -phenylethylester),"Dimepiperate" or AMY-93 "(PM, pp. 404-405) (= piperidine-1-thiocarboxylic acid S-1-methyl-1-phenylethyl ester),
„Daimuron" oder ASK 23" (PM, S. 330) (= 1-(1 -Methyl-1 -phenylethyl)-3-p- tolyl-hamstoff),"Daimuron" or ASK 23 "(PM, p. 330) (= 1- (1-methyl-1-phenylethyl) -3-p-tolylurea),
„Cumyluron" = AJC-940" (= 3-(2-Chlorphenylmethyl)-1-(1 -methyl-1 -phenyl- ethyl)-harnstoff, siehe JP-A-60087254),"Cumyluron" = AJC-940 "(= 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254),
„Methoxyphenon" oder ANK 049" (= 3,3'-Dimethyl-4-methoxy- benzophenon),"Methoxyphenone" or ANK 049 "(= 3,3'-dimethyl-4-methoxybenzophenone),
„CSB" (= 1-Brom-4-(chlormethylsulfonyl)-benzol) (CAS-Reg. Nr. 54091-06-4 von Kumiai)."COD" (= 1-bromo-4- (chloromethylsulfonyl) benzene) (CAS Reg. No. 54091-06-4 by Kumiai).
Die Wirkstoffe (A) sind, gegebenenfalls in Gegenwart von Safenern, zur Bekämpfung von Schadpflanzen in Pflanzen kulturen geeignet, beispielsweise in wirtschaftlich bedeutenden Kulturen wie Getreide (z.B. Weizen, Gerste, Roggen, Hafer, Reis, Mais, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja. Von besonderem Interesse ist dabei die Anwendung in dikotylen Kulturen wie Zuckerrübe, Raps, Baumwolle und Soja. Für die Kombinationen (A)+(B) sind diese Kulturen ebenfalls bevorzugt. Als Kombinationspartner (B) kommen folgende Verbindungen der Untergruppen (B1 ) bis (B3) in Frage (die Bezeichnung der Herbizide erfolgt weitgehend mit dem „common name", soweit möglich nach der Referenzstelle "The Pesticide Manual" 11th Ed., British Crop Protection Council 1997, abgekürzt „PM"):The active ingredients (A) are suitable, if appropriate in the presence of safeners, for controlling harmful plants in crops, for example in economically important crops such as cereals (for example wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, Rapeseed, cotton and soy. Of particular interest is the use in dicotyledon crops such as sugar beet, rapeseed, cotton and soy. These cultures are also preferred for the combinations (A) + (B). The following compounds of subgroups (B1) to (B3) are suitable as combination partners (B) (the herbicides are largely designated by the "common name", if possible according to the reference point "The Pesticide Manual" 11th Ed., British Crop Protection Council 1997, abbreviated "PM"):
(B1 ) Selektiv in einigen dikotylen Kulturen gegen monokotyle und dikotyle(B1) Selective in some dicot cultures against monocot and dicot
Schadpflanzen wirksame Herbizide, ausgewählt aus der Gruppe bestehend ausHerbicides active against harmful plants, selected from the group consisting of
a) in Zuckerrübe selektive Herbizide, ausgewählt aus der Gruppe bestehend ausa) in sugar beet selective herbicides selected from the group consisting of
(B1.1 ) Ethofumesate (PM, S. 484-486), d. h. Methansulfonsäure-(2- ethoxy-2,3 dihydro-3,3-dimethylbenzofuran-5-yl)-ester;(B1.1) Ethofumesate (PM, pp. 484-486), d. H. Methanesulfonic acid (2-ethoxy-2,3 dihydro-3,3-dimethylbenzofuran-5-yl) ester;
(B1.2) Chloridazon (PM, S. 215-216), d. h. 5-Amino-4-chlor-2-phenyl- pyridazin-3(2H)-on;(B1.2) Chloridazon (PM, pp. 215-216), i.e. H. 5-amino-4-chloro-2-phenylpyridazin-3 (2H) -one;
(B1.3) Triflusulfuron und dessen Ester, wie der Methylester, (PM, S. 1250-1252), d.h. 2-[4-(Dimethylamino)-6-(2,2,2-trifluorethoxy)- 1 ,3,5-triazin-2-yl]-carbamoylsulfamoyl]-6-methyl-benzoesäure bzw. -methylester;(B1.3) triflusulfuron and its esters, such as the methyl ester, (PM, pp. 1250-1252), i.e. 2- [4- (dimethylamino) -6- (2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl] carbamoylsulfamoyl] -6-methylbenzoic acid or methyl ester;
(B1.4) Metamitron (PM, S. 799-801 ), d.h. 4-Amino-4,5-dihydro-3- methyl-6-phenyl-1 ,2,4-triazin-5-on;(B1.4) Metamitron (PM, pp. 799-801), i.e. 4-amino-4,5-dihydro-3-methyl-6-phenyl-1, 2,4-triazin-5-one;
b) in Raps selektive Herbizide, ausgewählt aus der Gruppe bestehend ausb) in rape selective herbicides selected from the group consisting of
(B1.5) Metazachlor (PM, S. 801-803), d. h. 2-Chlor-N-(2,6- dimethylphenyl)-N-(1 H-pyrazol-1 -ylmethyl)-acetanilid;(B1.5) Metazachlor (PM, pp. 801-803), d. H. 2-chloro-N- (2,6-dimethylphenyl) -N- (1 H-pyrazol-1-ylmethyl) acetanilide;
(B1.6) Napropamide (PM, S. 866-868), d. h. (R,S)-N,N-Diethyl-2-(1- naphthyloxy)-propanamid;(B1.6) Napropamide (PM, pp. 866-868), d. H. (R, S) -N, N-diethyl-2- (1-naphthyloxy) propanamide;
(B1.7) Carbetamide (PM, S. 184-185), d. h. (R)-Carbanilinsäure-I- (ethylcarbamoyl)-ethylester;(B1.7) carbetamides (PM, pp. 184-185), d. H. (R) -carbanilic acid I- (ethylcarbamoyl) ethyl ester;
(B1.8) Dimefuron (PM, S. 403-404), d. h. 3-[4-(5-tert.-Butyl-2,3-dihydro- 2-oxo-l ,3,4-oxadiazol-3-yl)-3-chlorphenyl]-N,N- dimethylharnstoff; (B1.9) Dimethachlor (PM, S. 406-407), 2-Chlor-N-(2,6-dimethylphenyl)- N-(2-methoxyethyl)-aceto-2',6'-xylilid;(B1.8) Dimefuron (PM, pp. 403-404), ie 3- [4- (5-tert-butyl-2,3-dihydro- 2-oxo-l, 3,4-oxadiazol-3-yl) -3-chlorophenyl] -N, N-dimethylurea; (B1.9) dimethachlor (PM, pp. 406-407), 2-chloro-N- (2,6-dimethylphenyl) - N- (2-methoxyethyl) aceto-2 ', 6'-xylilide;
c) in Baumwolle selektive Herbizide ausgewählt aus der Gruppe bestehend ausc) in cotton selective herbicides selected from the group consisting of
(B1.10)Norflurazon (PM, S. 886-888), d. h. 4-Chlor-5-(methylamino)-2- [3-(trifluormethyl)-phenyl]-3-(2H)-pyhdazinon;(B1.10) Norflurazon (PM, pp. 886-888), d. H. 4-chloro-5- (methylamino) -2- [3- (trifluoromethyl) phenyl] -3- (2H) pyhdazinone;
(B1.11 )Fluometuron (auch "Meturon", PM, S. 578-579), d. h. N,N- Dimethyl-N'-[3-(trifluormethyl)-phenyl]-harnstoff;(B1.11) Fluometuron (also "Meturon", PM, pp. 578-579), i.e. H. N, N-dimethyl-N '- [3- (trifluoromethyl) phenyl] urea;
(B1.12)Methylarsonsäure der Formel CH3As(=O)(OH)2 und deren(B1.12) methylarsonic acid of the formula CH3As (= O) (OH) 2 and their
Salze wie DSMA = Dinatriumsalz oder MSMA =Salts like DSMA = disodium salt or MSMA =
Mononatriumsalz von Methylarsonsäure (PM, S. 821-823); (B1.13)Diuron (PM, S. 443-445), d. h. 3-(3,4-Dichlorphenyl)-1 ,1- dimethyl-harnstoff; (B1.14)Prometryn (Promethyrin) (PM, S. 1011-1013), d. h. N,N'-Bis(1- methylethyl)-6-methylthio)-2,4-diamino-1 ,3,5-triazin;Monosodium salt of methylarsonic acid (PM, pp. 821-823); (B1.13) Diuron (PM, pp. 443-445), d. H. 3- (3,4-dichlorophenyl) -1, 1-dimethyl-urea; (B1.14) Prometryn (Promethyrin) (PM, pp. 1011-1013), d. H. N, N'-bis (1-methylethyl) -6-methylthio) -2,4-diamino-1, 3,5-triazine;
d) in Soja selektive Herbizide ausgewählt aus der Gruppe bestehend aus (B1.15)Trifluralin (PM, S. 1248-1250), d.h. α,α,α-trifluoro-2,6-dinitro-d) in soybean selective herbicides selected from the group consisting of (B1.15) trifluralin (PM, pp. 1248-1250), i.e. α, α, α-trifluoro-2,6-dinitro-
N,N-dipropyl-p-toluol; (B1.16)Sulfentrazone (PM, S. 1126-1127), d.h. 2',4'-dichloro-5'-(4- difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1 ,2,4-triazol-1- yl)methansulfonanilid; (B1.17)Ethalfluralin (PM, S. 473-474), d.h. N-ethyl- ,α, -trifluoro-N-(2- methylallyl)-2,6-dinitro-p-toluol; (B1.18)Vernolate (PM, S. 1264-1266), d.h. S-propyl dipropylthiocarbamat; (B1.19)Flumioxazin (PM, S. 576-577), d.h. N-(7-fluoro-3,4-dihydro-3- oxo-4-prop-2-ynyl-2H-1 ,4-benzoxazin-6-yl)cyclohex-1-ene-1 ,2- dicarboxamid;N, N-dipropyl-p-toluene; (B1.16) Sulfentrazone (PM, p. 1126-1127), ie 2 ', 4'-dichloro-5' - (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H- 1, 2,4-triazol-1-yl) methanesulfonanilide; (B1.17) ethalfluralin (PM, pp. 473-474), ie N-ethyl-, α, -trifluoro-N- (2-methylallyl) -2,6-dinitro-p-toluene; (B1.18) Vernolate (PM, pp. 1264-1266), ie S-propyl dipropylthiocarbamate; (B1.19) flumioxazin (PM, pp. 576-577), ie N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin- 6-yl) cyclohex-1-ene-1, 2- dicarboxamide;
(B2) Selektiv in einigen dikotylen Kulturen überwiegend gegen dikotyle(B2) Selective in some dicotyledon cultures predominantly against dicotyledons
Schadpflanzen wirksame Herbizide, ausgewählt aus der Gruppe bestehend aus, a) in Zuckerrübe selektive Herbizide ausgewählt aus der Gruppe bestehend ausHerbicides active on harmful plants, selected from the group consisting of: a) herbicides selective in sugar beet selected from the group consisting of
(B2.1 ) Desmedipham (PM, S. 349-350), d.h., N-[3-(B2.1) Desmedipham (PM, pp. 349-350), i.e., N- [3-
(Ethoxycarbonylamino)phenyl]-carbaminsäure-phenyl-ester; (B2.2) Phenmedipham(PM, S. 948-949), d.h. N-[3-(Ethoxycarbonylamino) -phenyl] -carbamic acid phenyl ester; (B2.2) Phenmedipham (PM, pp. 948-949), i.e. N- [3-
(Methoxycarbonylamino)phenyl]-carbaminsäure-3- methylphenyl-ester; (B2.3) Quinmerac (PM, S. 1080-1082), d.h., 7-Chlor-3-methyl-chiπolin-(Methoxycarbonylamino) phenyl] carbamic acid 3-methylphenyl ester; (B2.3) Quinmerac (PM, pp. 1080-1082), i.e. 7-chloro-3-methyl-chiolin-
8-carbonsäure;8-carboxylic acid;
b) in Raps selektive Herbizide ausgewählt aus der Gruppe bestehend aus (B2.4) Clopyralid (PM, S. 260-263), d. h. 3,6-Dichlorpyridin-2- carbonsäure und deren Salze; (B2.5) Pyridate (PM, S. 1064-1066), d. h. O-(6-Chlor-3- phenylpyridazin-4-yl)-S-octyl-thiocarbonat; (B2.6) Ethametsulfuron-methyl (PM, S. 475-476), d. h. 2-{N-[N-(4-b) in rapeseed selective herbicides selected from the group consisting of (B2.4) clopyralid (PM, pp. 260-263), d. H. 3,6-dichloropyridine-2-carboxylic acid and its salts; (B2.5) Pyridate (PM, pp. 1064-1066), d. H. O- (6-chloro-3-phenylpyridazin-4-yl) -S-octylthiocarbonate; (B2.6) Ethametsulfuron-methyl (PM, pp. 475-476), d. H. 2- {N- [N- (4-
Ethoxy-6-methylamino-1 ,3,5-triazin-2-yl)-aminocarbonyl]- aminosulfonylj-benzoesäuremethylester;Ethoxy-6-methylamino-1, 3,5-triazin-2-yl) aminocarbonyl] - aminosulfonylj-benzoic acid methyl ester;
c) in Baumwolle selektive Herbizide ausgewählt aus der Gruppe bestehend ausc) in cotton selective herbicides selected from the group consisting of
(B2.7) Pyrithiobac und dessen Salze, z. B. das Natriumsalz, (PM, S. 1073-1075), d. h. 2-Chlor-6-(4,6-dimethoxypyrimidin-2-ylthio)- benzoesäure-natriumsalz;(B2.7) pyrithiobac and its salts, e.g. B. the sodium salt, (PM, pp. 1073-1075), d. H. 2-chloro-6- (4,6-dimethoxypyrimidin-2-ylthio) benzoic acid sodium salt;
d) in Soja selektive Herbizide ausgewählt aus der Gruppe bestehend aus (B2.8) Oxyfluorfen (PM, S. 919-921 ), d.h. 2-chloro-α,α,α-trifluoro-p-tolyld) in soybean selective herbicides selected from the group consisting of (B2.8) Oxyfluorfen (PM, pp. 919-921), ie 2-chloro-α, α, α-trifluoro-p-tolyl
3-ethoxy-4-nitrophenyl ether; (B2.9)Fomesafen (PM, S. 616-618), d.h. 5-(2-chloro-α,α,α-trifluoro-p- tolyloxyl)-N-methylsulfonyl-2-nitrobenzamid; (B2.10)Flumiclorac (PM, S. 575-576), d.h. [2-chloro-5-(cyclohex-1-ene-3-ethoxy-4-nitrophenyl ether; (B2.9) Fomesafen (PM, pp. 616-618), i.e. 5- (2-chloro-α, α, α-trifluoro-p-tolyloxyl) -N-methylsulfonyl-2-nitrobenzamide; (B2.10) Flumiclorac (PM, pp. 575-576), i.e. [2-chloro-5- (cyclohex-1-ENE-
1 ,2-dicarboximido)-4-fluorophenoxy]essigsäure, und dessen1, 2-dicarboximido) -4-fluorophenoxy] acetic acid, and its
Ester wie der Pentylester; (B2.11 )2,4-DB (PM, S. 337-339), d.h. 4-(2,4- dichlorophenoxy)buttersäure, und dessen Ester und Salze; (B2.12)Diclosulam (vgl. AG CHEM New Compound Review, Vol. 17,Esters such as the pentyl ester; (B2.11) 2,4-DB (PM, pp. 337-339), i.e. 4- (2,4-dichlorophenoxy) butyric acid, and its esters and salts; (B2.12) Diclosulam (see AG CHEM New Compound Review, Vol. 17,
(1999) Seite 37, triazolopyrimidin-sulfonanilid-Herbizid);(1999) page 37, triazolopyrimidine sulfonanilide herbicide);
(B2.13)Oxasulfuron (PM, S. 911-912), d.h. oxetan-3-yl 2-[(4,6- dimethylpyrimidin-2-yl)-carbamoylsulfamoyl]benzoat;(B2.13) Oxasulfuron (PM, pp. 911-912), i.e. oxetan-3-yl 2 - [(4,6-dimethylpyrimidin-2-yl) carbamoylsulfamoyl] benzoate;
(B3) Selektiv in einigen dikotylen Kulturen überwiegend gegen monokotyle(B3) Selective against monocotyledons in some dicotyledon cultures
Schadpflanzen wirksame Herbizide, ausgewählt aus der Gruppe bestehend ausHerbicides active against harmful plants, selected from the group consisting of
(B3.1 ) Profluazol (AGROW, No. 338 October 15th, 1999, S. 26, PJB Publications Ltd. 1999, WO 97/15576), d.h. 1-chloro-N-[2- chloro-4-fluoro-5-[(6S, 7aR)-6-fluorotetrahydro-1 ,3-dioxo-1 H- pyrrolo[1 ,2-c]imidazol-2(3H)-yl]phenyl]-methansulfonamid;(B3.1) profluazol (AGROW, No. 338 October 15 th, 1999, p 26, PJB Publications Ltd. 1999, WO 97/15576), or 1-chloro-N- [2- chloro-4-fluoro- 5 - [(6S, 7aR) -6-fluorotetrahydro-1, 3-dioxo-1 H-pyrrolo [1, 2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide;
B3.2) Amicarbazone (AGROW, No. 338 October 15th, 1999, S. 26, PJB Publications Ltd. 1999, DE 3839206), d.h. 4-amino-N-(1 ,1- dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo-1 H-1 ,2,4- triazol-1 -carboxamid);B3.2) Amicarbazone (AGROW, No. 338 October 15 th , 1999, p. 26, PJB Publications Ltd. 1999, DE 3839206), ie 4-amino-N- (1, 1-dimethylethyl) -4,5-dihydro-3- (1-methylethyl) -5-oxo-1 H-1, 2,4-triazole- 1-carboxamide);
B3.3) Pyriftalid (AGROW, No. 338 October 15,h, 1999, S. 26, PJBB3.3) Pyriftalid (AGROW, No. 338 October 15 , h , 1999, p. 26, PJB
Publications Ltd. 1999, WO 91/05781 ), d.h. 7-[(4,6-dimethoxy-2- pyrimidinyl)thio]-3-methyl-1(3H)-isobenzofuranon;Publications Ltd. 1999, WO 91/05781), i.e. 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H) -isobenzofuranone;
B3.4) Trifloxysulfuron und dessen Salze, z.B. das Natriumsalz,B3.4) trifloxysulfuron and its salts, e.g. the sodium salt,
(AGROW, No. 338 October 15th, 1999, S. 26, PJB Publications Ltd. 1999, WO 92/16522), d.h. N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2- pyridinesulfonamid;(AGROW, No. 338 October 15 th, 1999, p 26, PJB Publications Ltd. 1999, WO 92/16522), that N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3 - (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide;
B3.5) Epocholeone (AGROW, No. 338 October 15,h, 1999, S. 26, PJB Publications Ltd. 1999, WO 94/28011 ), d.h. 1-[(1S)-1-[(2R, 3R)- 3-[(1 S)-1 -ethyl-2-methylpropyl]oxiranyl]ethyl]hexadeca-hydro- 10a,12a-dimethyl-8,9-bis(1-oxopropoxy)-(1 R, 3aS, 3bS, 6aS, 8S, 9R, 10aR, 10bS, 12aS)-6H-Benz[c]indeno[5,4-e]oxepin-6- one;B3.5) Epocholeone (AGROW, No. 338 October 15 , h , 1999, p. 26, PJB Publications Ltd. 1999, WO 94/28011), ie 1 - [(1S) -1 - [(2R, 3R) - 3 - [(1 S) -1-ethyl-2-methylpropyl] oxiranyl] ethyl] hexadeca-hydro-10a, 12a-dimethyl-8,9-bis (1-oxopropoxy) - (1 R, 3aS, 3bS, 6aS, 8S, 9R, 10aR, 10bS, 12aS) -6H-Benz [c] indeno [5,4-e] oxepin-6-one;
B3.6) Tepraloxydim (DE 4222261 ), d.h. 2-[1-[[[(2E)-3-chloro-2- propenyl]oxy]imino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4- yl)-2-cyclohexen-1 -on;B3.6) Tepraloxydim (DE 4222261), i.e. 2- [1 - [[[(2E) -3-chloro-2-propenyl] oxy] imino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1 -one;
Wenn die Kurzform des „common name" verwendet wird, so sind damit alle gängigen Derivate, wie die Ester und Salze, und Isomere, insbesondere optische Isomere umfaßt, insbesondere die handelsüblichen Form bzw. Formen. Die angegebenen chemischen Verbindungsnamen bezeichnen zumindest eine der von dem „common name" umfaßten Verbindungen, häufig eine bevorzugte Verbindung. Bei Sulfonylharnstoffen sind mit Salzen auch die umfaßt, die durch Austausch eines Wasserstoffatoms an der Sulfonamidgruppe durch ein Kation entstehen.If the short form of the "common name" is used, all common derivatives, such as the esters and salts, and isomers, in particular optical isomers, are included, in particular the commercial form or forms. The chemical compound names given denote at least one of those "Common name" included connections, often a preferred connection. In the case of sulfonylureas, salts are also included which are formed by the replacement of a hydrogen atom on the sulfonamide group by a cation.
Bevorzugt sind Herbizid-Kombinationen aus einer oder mehreren Verbindungen (A) mit einer oder mehreren Verbindungen der Gruppe (B1 ) oder (B2) oder (B3). Weiter bevorzugt sind Kombinationen von Verbindungen (A) mit einer oder mehreren Verbindungen (B) nach dem Schema:Herbicide combinations of one or more compounds (A) with one or more compounds of group (B1) or (B2) or (B3) are preferred. Combinations of compounds (A) with one or more compounds (B) according to the scheme are further preferred:
(A) + (B1 ) + (B2), (A) + (B1 ) + (B3), (A) + (B2) + (B3) oder (A) + (B1 ) + (B2) +(B3)(A) + (B1) + (B2), (A) + (B1) + (B3), (A) + (B2) + (B3) or (A) + (B1) + (B2) + (B3 )
Dabei sind auch solche Kombinationen erfindungsgemäß, denen noch ein oder mehrere weitere agrochemische Wirkstoffe anderer Struktur [Wirkstoffe (C)] zugesetzt werden wieCombinations according to the invention to which one or more further agrochemical active substances of other structure [active substances (C)] are added are also according to the invention
(A)+ (B1) + (C), (A)+ (B2) + (C) oder (A) + (B3) + (C),(A) + (B1) + (C), (A) + (B2) + (C) or (A) + (B3) + (C),
(A) + (B1 ) + (B2) + (C), (A) + (B1 ) + (B3) + (C), (A) + (B2) + (B3) + (C) oder(A) + (B1) + (B2) + (C), (A) + (B1) + (B3) + (C), (A) + (B2) + (B3) + (C) or
(A) + (B1) + (B2)+(B3) + (C).(A) + (B1) + (B2) + (B3) + (C).
Für Kombinationen der letztgenannten Art mit drei oder mehr Wirkstoffen gelten die nachstehend insbesondere für erfindungsgemäßen Zweierkombinationen erläuterten bevorzugten Bedingungen in erster Linie ebenfalls, sofern darin die erfindungsgemäßen Zweierkombinationen enthalten sind und bezüglich der betreffenden Zweierkombination.For combinations of the latter type with three or more active substances, the preferred conditions explained below, in particular for combinations of two according to the invention, also primarily apply, provided that the combinations of two according to the invention are contained therein and with regard to the combination of two concerned.
Von besonderem Interesse ist die Anwendung von herbiziden Mitteln mit einem Gehalt an folgenden Verbindungen (A) + (B):Of particular interest is the use of herbicidal compositions containing the following compounds (A) + (B):
(A1.1) + (B1.1), (A1.1) + (B1.2), (A1.1) + (B1.3), (A1.1) + (B1.4),(A1.1) + (B1.1), (A1.1) + (B1.2), (A1.1) + (B1.3), (A1.1) + (B1.4),
(A1.1) + (B1.5), (A1.1) + (B1.6), (A1.1) + (B1.7), (A1.1) + (B1.8),(A1.1) + (B1.5), (A1.1) + (B1.6), (A1.1) + (B1.7), (A1.1) + (B1.8),
(A1.1 ) + (B1.9), (A1.1 ) + (B1.10), (A1.1 ) + (B1.11 ), (A1.1 ) + (B1.12),(A1.1) + (B1.9), (A1.1) + (B1.10), (A1.1) + (B1.11), (A1.1) + (B1.12),
(A1.1) + (B1.13), (A1.1) + (B1.14), (A1.1) + (B1.15), (A1.1) + (B1.16),(A1.1) + (B1.13), (A1.1) + (B1.14), (A1.1) + (B1.15), (A1.1) + (B1.16),
(A1.1) + (B1.17), (A1.1) + (B1.18), (A1.1) + (B1.19),(A1.1) + (B1.17), (A1.1) + (B1.18), (A1.1) + (B1.19),
(A1.1) + (B2.1), (A1.1) + (B2.2.), (A1.1) + (B2.3), (A1.1) + (B2.4),(A1.1) + (B2.1), (A1.1) + (B2.2.), (A1.1) + (B2.3), (A1.1) + (B2.4),
(A1.1) + (B2.5), (A1.1) + (B2.6), (A1.1) + (B2.7), (A1.1) + (B2.8),(A1.1) + (B2.5), (A1.1) + (B2.6), (A1.1) + (B2.7), (A1.1) + (B2.8),
(A1.1) + (B2.9), (A1.1) + (B2.10), (A1.1) + (B2.11), (A1.1) + (B2.12),(A1.1) + (B2.9), (A1.1) + (B2.10), (A1.1) + (B2.11), (A1.1) + (B2.12),
(A1.1) + (B2.13),(A1.1) + (B2.13),
(A1.1) + (B3.1), (A1.1) + (B3.2), (A1.1) + (B3.3), (A1.1) + (B3.4),(A1.1) + (B3.1), (A1.1) + (B3.2), (A1.1) + (B3.3), (A1.1) + (B3.4),
(A1.1) + (B3.5), (A1.1) + (B3.6), (A1.2 B1.1 ), A1.2) + (B1.2), (A1.2) + (B1.3), (A1.2) + (B1.4), (A1.2 B1.5), A1.2) + (B1.6), (A1.2) + (B1.7), (A1.2) + (B1.8), (A1.2 B1.9), A1.2) + (B1.10), (A1.2) + (B1.11 ), (A1.2) + (B1.12), (A1.2 B1.13) (A1.2) + (B1.14), (A1.2) + (B1.15), (A1.2) + (B1.16), (A1.2 B1.17) (A1.2) + (B1.18), (A1.2) + (B1.19), (A1.2 B2.1 ), A1.2) + (B2.2.), (A1.2) + (B2.3), (A1.2) + (B2.4), (A1.2 B2.5), A1.2) + (B2.6), (A1.2) + (B2.7), (A1.2) + (B2.8), (A1.2 B2.9), A1.2) + (B2.10), (A1.2) + (B2.11 ), (A1.2) + (B2.12), (A1.2 B2.13) (A1.2 B3.1 ), A1.2) + (B3.2), (A1.2) + (B3.3), (A1.2) + (B3.4) (A1.2 B3.5), A1.2) + (B3.6),(A1.1) + (B3.5), (A1.1) + (B3.6), (A1.2 B1.1), A1.2) + (B1.2), (A1.2) + (B1.3), (A1.2) + (B1.4), (A1.2 B1. 5), A1.2) + (B1.6), (A1.2) + (B1.7), (A1.2) + (B1.8), (A1.2 B1.9), A1.2 ) + (B1.10), (A1.2) + (B1.11), (A1.2) + (B1.12), (A1.2 B1.13) (A1.2) + (B1.14 ), (A1.2) + (B1.15), (A1.2) + (B1.16), (A1.2 B1.17) (A1.2) + (B1.18), (A1.2 ) + (B1.19), (A1.2 B2.1), A1.2) + (B2.2.), (A1.2) + (B2.3), (A1.2) + (B2. 4), (A1.2 B2.5), A1.2) + (B2.6), (A1.2) + (B2.7), (A1.2) + (B2.8), (A1. 2 B2.9), A1.2) + (B2.10), (A1.2) + (B2.11), (A1.2) + (B2.12), (A1.2 B2.13) ( A1.2 B3.1), A1.2) + (B3.2), (A1.2) + (B3.3), (A1.2) + (B3.4) (A1.2 B3.5) , A1.2) + (B3.6),
(A1.5 B1.1 ), A1.5) + (B1.2), (A1.5) + (B1.3), (A1.5) + (B1.4), (A1.5 B1.5), A1.5) + (B1.6), (A1.5) + (B1.7), (A1.5) + (B1.8), (A1.5 B1.9), A1.5) + (B1.10), (A1.5) + (B1.11 ), (A1.5) + (B1.12), (A1.5 B1.13) (A1.5) + (B1.14), (A1.5) + (B1.15), (A1.5) + (B1.16), (A1.5 B1.17) (A1.5) + (B1.18), (A1.5) + (B1.19), (A1.5 B2.1 ), A1.5) + (B2.2.), (A1.5) + (B2.3), (A1.5) + (B2.4), (A1.5 B2.5), A1.5) + (B2.6), (A1.5) + (B2.7), (A1.5) + (B2.8), (A1.5 B2.9), A1.5) + (B2.10), (A1.5) + (B2.11 ), (A1.5) + (B2.12), (A1.5 B2.13) (A1.5 B3.1 ), A1.5) + (B3.2), (A1.5) + (B3.3), (A1.5) + (B3.4) (A1.5 B3.5), A1.5) + (B3.6),(A1.5 B1.1), A1.5) + (B1.2), (A1.5) + (B1.3), (A1.5) + (B1.4), (A1.5 B1. 5), A1.5) + (B1.6), (A1.5) + (B1.7), (A1.5) + (B1.8), (A1.5 B1.9), A1.5 ) + (B1.10), (A1.5) + (B1.11), (A1.5) + (B1.12), (A1.5 B1.13) (A1.5) + (B1.14 ), (A1.5) + (B1.15), (A1.5) + (B1.16), (A1.5 B1.17) (A1.5) + (B1.18), (A1.5 ) + (B1.19), (A1.5 B2.1), A1.5) + (B2.2.), (A1.5) + (B2.3), (A1.5) + (B2. 4), (A1.5 B2.5), A1.5) + (B2.6), (A1.5) + (B2.7), (A1.5) + (B2.8), (A1. 5 B2.9), A1.5) + (B2.10), (A1.5) + (B2.11), (A1.5) + (B2.12), (A1.5 B2.13) ( A1.5 B3.1), A1.5) + (B3.2), (A1.5) + (B3.3), (A1.5) + (B3.4) (A1.5 B3.5) , A1.5) + (B3.6),
(A2.1 B1.1 ), (A2.1 + (B1.2), (A2.1 ) + (B1.3), (A2.1 ) + (B1.4), (A2.1 B1.5), (A2.1 + (B1.6), (A2.1 ) + (B1.7), (A2.1 ) + (B1.8), (A2.1 B1.9), (A2.1 + (B1.10), (A2.1 ) + (B1.11 ), (A2.1 ) + (B1.12), (A2.1 B1.13), (A2. ) + (B1.14), (A2.1 ) + (B1.15), (A2.1 ) + (B1.16), (A2.1 B1.17), (A2. ) + (B1.18), (A2.1) + (B1.19), (A2.1 B2.1 ), (A2.1 + (B2.2.), (A2.1 ) + (B2.3), (A2.1 ) + (B2.4), (A2.1 ) + (B2.5), (A2.1 ) + (B2.6), (A2.1 ) + (B2.7), (A2.1 ) + (B2.8), (A2.1 ) + (B2.9), (A2.1 ) + (B2.10), (A2.1 ) + (B2.11 ), (A2.1 ) + (B2.12), (A2.1 ) + (B2.13),(A2.1 B1.1), (A2.1 + (B1.2), (A2.1) + (B1.3), (A2.1) + (B1.4), (A2.1 B1. 5), (A2.1 + (B1.6), (A2.1) + (B1.7), (A2.1) + (B1.8), (A2.1 B1.9), (A2. 1 + (B1.10), (A2.1) + (B1.11), (A2.1) + (B1.12), (A2.1 B1.13), (A2.) + (B1.14 ), (A2.1) + (B1.15), (A2.1) + (B1.16), (A2.1 B1.17), (A2.) + (B1.18), (A2.1 ) + (B1.19), (A2.1 B2.1), (A2.1 + (B2.2.), (A2.1) + (B2.3), (A2.1) + (B2. 4) (A2.1) + (B2.5), (A2.1) + (B2.6), (A2.1) + (B2.7), (A2.1) + (B2.8), (A2 .1) + (B2.9), (A2.1) + (B2.10), (A2.1) + (B2.11), (A2.1) + (B2.12), (A2.1 ) + (B2.13),
(A2.1 ) + (B3.1 ), (A2.1 ) + (B3.2), (A2.1 ) + (B3.3), (A2.1 ) + (B3.4) (A2.1 ) + (B3.5), (A2.1 ) + (B3.6),(A2.1) + (B3.1), (A2.1) + (B3.2), (A2.1) + (B3.3), (A2.1) + (B3.4) (A2. 1) + (B3.5), (A2.1) + (B3.6),
Dabei sind die oben genannten Aufwandmengenbereiche und Aufwandmengenverhältnisse jeweils bevorzugt.The above-mentioned application rate ranges and application rate ratios are preferred in each case.
In Einzelfällen kann es sinnvoll sein, eine oder mehrere, vorzugsweise eine der Verbindungen (A) mit mehreren Verbindungen (B) aus den Klassen (B1 ), (B2) und (B3) zu kombinieren.In individual cases, it may make sense to combine one or more, preferably one of the compounds (A) with several compounds (B) from classes (B1), (B2) and (B3).
Weiterhin können die erfindungsgemäßen Kombinationen zusammen mit anderen agrochemischen Wirkstoffen beispielsweise aus der Gruppe der Safener, Fungizide, Insektizide und Pflanzenwachstumsregulatoren oder im Pflanzenschutz üblichen Zusatzstoffen und Formulierungshilfsmittel eingesetzt werden. Zusatzstoffe sind beispielsweise Düngemittel und Farbstoffe.Furthermore, the combinations according to the invention can be used together with other agrochemical active ingredients, for example from the group of safeners, fungicides, insecticides and plant growth regulators or additives and formulation auxiliaries customary in crop protection. Additives include fertilizers and dyes.
Die erfindungsgemäßen Kombinationen (= herbiziden Mittel) weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen auf. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Dabei ist es gleichgültig, ob die Substanzen im Vorsaat-, Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Bevorzugt ist die Anwendung im Nachauflaufverfahren oder im frühen Nachsaat-Vorauflaufverfahren.The combinations according to the invention (= herbicidal compositions) have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence. Use in the post-emergence process or in the early post-sowing pre-emergence process is preferred.
Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne daß durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.In particular, some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned, which can be controlled by the compounds according to the invention, without being limited to certain by the name Species should be done.
Auf der Seite der monokotylen Unkrautarten werden z.B. Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. sowie Cyperusarten aus der annuellen Gruppe und auf Seiten der perennierenden Spezies Agropyron, Cynodon, Imperata sowie Sorghum und auch ausdauernde Cyperusarten gut erfaßt.On the side of the monocot weed species, e.g. Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. as well as Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum as well as perennial Cyperus species.
Bei dikotylen Unkrautarten erstreckt sich das Wirkungsspektrum auf Arten wie z.B. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp.,Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. und Viola spp., Xanthium spp., auf der annuellen Seite sowie Convolvulus, Cirsium, Rumex und Artemisia bei den perennierenden Unkräutern.With dicotyledon weed species, the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp ., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., on the annual side, and convolvulus, cirsium, rumex and artemisia in the perennial weeds.
Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab.If the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
Bei Applikation der Wirkstoffe auf die grünen Pfianzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so daß auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird.When the active ingredients are applied to the green plant parts in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the crop plants harmful weed competition is eliminated very early and sustainably.
Die erfindungsgemäßen herbiziden Mittel zeichnen sich durch eine schnell einsetzende und lang andauernde herbizide Wirkung aus. Die Regenfestigkeit der Wirkstoffe in den erfindungsgemäßen Kombinationen ist in der Regel günstig. Als besonderer Vorteil fällt ins Gewicht, daß die in den Kombinationen verwendeten und wirksamen Dosierungen von Verbindungen (A) und (B) so gering eingestellt werden kann, daß ihre Bodenwirkung optimal niedrig ist. Somit wird deren Einsatz nicht nur in empfindlichen Kulturen erst möglich, sondern Grundwasser-Kontaminationen werden praktisch vermieden. Durch die erfindungsgemäßen Kombination von Wirkstoffen wird eine erhebliche Reduzierung der nötigen Aufwandmenge der Wirkstoffe ermöglicht.The herbicidal compositions according to the invention are notable for a rapid onset and long-lasting herbicidal action. The rain resistance of the active ingredients in the combinations according to the invention is generally favorable. As A particular advantage is that the effective dosages of compounds (A) and (B) used in the combinations can be set so low that their soil effect is optimally low. This means that their use is not only possible in sensitive crops, but groundwater contamination is practically avoided. The combination of active substances according to the invention enables a considerable reduction in the necessary application rate of the active substances.
Bei der gemeinsamen Anwendung von Herbiziden des Typs (A)+(B) treten überadditive (= synergistische) Effekte auf. Dabei ist die Wirkung in den Kombinationen stärker als die zu erwartende Summe der Wirkungen der eingesetzten Einzelherbizide. Die synergistischen Effekte erlauben eine Reduzierung der Aufwandmenge, die Bekämpfung eines breiteren Spektrums von Unkräutern und Ungräsern, einen schnelleren Einsatz der herbiziden Wirkung, eine längere Dauerwirkung, eine bessere Kontrolle der Schadpflanzen mit nur einer bzw. wenigen Applikationen sowie eine Ausweitung des möglichen Anwendungszeitraumes. Teilweise wird durch den Einsatz der Mittel auch die Menge an schädlichen Inhaltsstoffen, wie Stickstoff oder Ölsäure, und deren Eintrag in den Boden reduziert.When herbicides of type (A) + (B) are used together, superadditive (= synergistic) effects occur. The effect in the combinations is stronger than the expected total of the effects of the individual herbicides used. The synergistic effects allow a reduction in the application rate, the control of a broad spectrum of weeds and weeds, a faster use of the herbicidal action, a longer lasting effect, better control of the harmful plants with only one or a few applications and an expansion of the possible application period. In some cases, the amount of harmful ingredients, such as nitrogen or oleic acid, and their entry into the soil is reduced through the use of the agents.
Die genannten Eigenschaften und Vorteile sind in der praktischen Unkrautbekämpfung gefordert, um landwirtschaftliche Kulturen von unerwünschten Konkurrenzpflanzen freizuhalten und damit die Erträge qualitativ und quantitativ zu sichern und/oder zu erhöhen. Der technische Standard wird durch diese neuen Kombinationen hinsichtlich der beschriebenen Eigenschaften deutlich übertroffen.The properties and advantages mentioned are required in practical weed control in order to keep agricultural crops free of undesired competing plants and thus to secure and / or increase the yields qualitatively and quantitatively. These new combinations significantly exceed the technical standard in terms of the properties described.
Obgleich die erfindungsgemäßen Kombinationen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Schadpflanzen aufweisen, werden die Kulturpflanzen nur unwesentlich oder gar nicht geschädigt. Darüberhinaus weisen die erfindungsgemäßen Mittel teilweise hervorragende wachstumsregulatorische Eigenschaften bei den Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da Emteverluste beim Lagern hierdurch verringert oder völlig verhindert werden können.Although the combinations according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all. In addition, some of the agents according to the invention have excellent growth-regulating properties in the crop plants. You grab regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, such as by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as losses in the harvest can be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatohschen Eigenschaften können die erfindungsgemäßen Mittel zur Bekämpfung von Schadpflanzen in gentechnisch veränderten oder durch Mutationsselektion erhaltenen Kulturpflanzen eingesetzt werden. Diese Kulturpflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, wie Resistenzen gegenüber herbiziden Mitteln oder Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind z.B. transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt.Because of their herbicidal and plant growth-regulating properties, the compositions according to the invention for controlling harmful plants can be used in genetically modified crops or crops obtained by mutation selection. These crop plants are generally distinguished by special advantageous properties, such as resistance to herbicidal agents or resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients. For example, Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten (siehe z.B. US 5,162,602; US 4,761 ,373; US 4,443,971 ). Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/11376, WO 92/14827, transgene Kulturpflanzen, welche Resistenzen gegen andere Herbizide aufweisen, beispielsweise gegen Sulfonylharnstoffe (EP-A-0257993, US-A-Conventional ways of producing new plants which have modified properties compared to previously occurring plants are, for example, classic breeding methods and the generation of mutants (see, for example, US Pat. No. 5,162,602; US Pat. No. 4,761,373; US Pat. No. 4,443,971). Alternatively, new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). In several cases, for example, genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, transgenic crop plants which are resistant to other herbicides, for example to sulfonylureas (EP-A-0257993, US-A-
5013659), transgene Kulturpflanzen, mit der Fähigkeit5013659), transgenic crops, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche dieBacillus thuringiensis toxins (Bt toxins) which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924,Making plants resistant to certain pests (EP-A-0142924,
EP-A-0193259). transgene Kulturpflanzen mit modifizierter FettsäurezusammensetzungEP-A-0193259). transgenic crops with modified fatty acid composition
(WO 91/13972).(WO 91/13972).
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt; siehe z.B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ).In principle, numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known; see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe der obengenannten Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden.For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffek.es oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet.The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense-RNA, a sense-RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically transcripts the above Gene product splits.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind.For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991 ), 95-106).When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
Die transgenen Pflanzenzelien können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen.The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants. Thus, transgenic plants are available which have changed properties due to overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Gegenstand der Erfindung ist weiterhin auch ein Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, vorzugsweise in Pflanzenkulturen wie Getreide (z.B. Weizen, Gerste, Roggen, Hafer, Reis, Mais, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, besonders bevorzugt in dikotylen Kulturen wie Zuckerrübe, Raps, Baumwolle und Soja, dadurch gekennzeichnet, daß man ein oder mehrere Herbizide des Typs (A) mit einem oder mehreren Herbiziden des Typs (B) auf die Schadpflanzen, Pflanzenteile, Pflanzensamen oder die Fläche auf der die Pflanzen wachsen, z.B. die Anbaufläche appliziert.The invention also relates to a process for controlling undesirable plant growth, preferably in crops such as cereals (for example wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, rape, cotton and soybeans, particularly preferably in dicotyledons Cultures such as sugar beet, rapeseed, cotton and soy, characterized in that one or several herbicides of type (A) with one or more herbicides of type (B) on the harmful plants, parts of plants, plant seeds or the area on which the plants grow, for example the area under cultivation.
Die Pflanzenkulturen können auch gentechnisch verändert oder durch Mutationsselektion erhalten sein und sind bevorzugt tolerant gegenüber Acetolactatsynthase (ALS)-Inhibitoren.The plant cultures can also be genetically modified or obtained by mutation selection and are preferably tolerant of acetolactate synthase (ALS) inhibitors.
Gegenstand der Erfindung ist auch die Verwendung der neuen Kombinationen aus Verbindungen (A)+(B) zur Bekämpfung von Schadpflanzen, vorzugsweise in Pflanzenkulturen.The invention also relates to the use of the new combinations of compounds (A) + (B) for controlling harmful plants, preferably in plant crops.
Die erfindungsgemäßen Wirkstoffkombinationen können sowohl als Mischformulierungen der zwei Komponenten (A) und (B), gegebenenfalls mit weiteren agrochemischen Wirkstoffen, Zusatzstoffen und/oder üblichen Formulierungshilfsmitteln vorliegen, die dann in üblicher weise mit Wasser verdünnt zur Anwendung gebracht werden, oder als sogenannte Tankmischungen durch gemeinsame Verdünnung der getrennt formulierten oder partiell getrennt formulierten Komponenten mit Wasser hergestellt werden.The active compound combinations according to the invention can be present both as mixed formulations of the two components (A) and (B), if appropriate with further agrochemical active compounds, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or as so-called tank mixes joint dilution of the separately formulated or partially separately formulated components with water.
Die Verbindungen (A) und (B) oder deren Kombinationen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemischphysikalischen Parameter vorgegeben sind. Als allgemeine Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), wäßrige Lösungen (SL), Emulsionen (EW) wie Öl-in-Wasser- und Wasser-in-ÖI-Emulsionen, versprühbare Lösungen oder Emulsionen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, Suspoemulsionen, Stäubemittel (DP), Beizmittel, Granulate zur Boden- oder Streuapplikation oder wasserdispergierbare Granulate (WG), ULV-Formulierungen, Mikrokapseln oder Wachse. Die einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker N.Y., 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.The compounds (A) and (B) or their combinations can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Examples of general formulation options are: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), dispersions based on oil or water, suspoemulsions, dusts (DP), mordants, granules for soil or litter application or water-dispersible granules (WG), ULV formulations, microcapsules or waxes. The individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker NY, 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridegewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986.The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J .; H. V. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, Detergents and Emulsifiers Annual, MC Publ. Corp., Ridegewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", volume 7, C. Hauser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen agrochemischen Wirkstoffen, wie anderen Herbiziden, Fungiziden, Insektiziden, sowie Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix.Based on these formulations, combinations with other agrochemical active ingredients, such as other herbicides, fungicides, insecticides, as well as safeners, fertilizers and / or growth regulators, can be prepared, e.g. in the form of a finished formulation or as a tank mix.
Spritzpulver (benetzbare Pulver) sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxethylierte Alkylphenole, polyethoxylierte Fettalkohole oder -Fettamine, Alkansulfonate oder Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'- dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten.Spray powders (wettable powders) are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or also oleoylmethyltauric acid sodium.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffs in einem organischen Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffe unter Zusatz von einem oder mehreren ionischen oder nichtionischen Tensiden (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calcium-Salze wie Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanfettsäureester, Polyoxyethylensorbitanfettsäureester oder Polyoxethylensorbitester.Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts, such as Ca-dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid ester sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene ethoxylate sorbet, polyoxyethylene ethoxylate or polyoxyethylene ethoxylate.
Stäubemittel erhält man durch Vermählen des Wirkstoffs mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde.Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate (SC) können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von weiteren Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden.Suspension concentrates (SC) can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding other surfactants, such as those e.g. already listed above for the other types of formulation.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls von weiteren Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen.Emulsions, e.g. Oil-in-water emulsions (EW) can, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally other surfactants, such as those e.g. already listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffs auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57.Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be used in the manner customary for the production of fertilizer granules. if desired in a mixture with fertilizers - granulated. Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of plate, fluidized bed, extruder and spray granules, see, for example, the process in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103.For more details on the formulation of crop protection products see e.g. G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pages 81-96, and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Formulierungen enthalten in der Regel 0,1 bis 99The agrochemical formulations usually contain 0.1 to 99
Gewichtsprozent, insbesondere 2 bis 95 Gew.-%, Wirkstoffe der Typen A und/oder% By weight, in particular 2 to 95% by weight, of active substances of types A and / or
B, wobei je nach Formulierungsart folgende Konzentrationen üblich sind:B, the following concentrations being customary depending on the type of formulation:
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 95 Gew.-%, derThe active substance concentration in wettable powders is e.g. about 10 to 95% by weight of the
Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration z.B. 5 bis 80 Gew.-%, betragen.The remainder to 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can e.g. 5 to 80% by weight.
Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen etwa 0,2 bis 25 Gew.-% Wirkstoff. Bei Granulaten wie dispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilsmittel und Füllstoffe verwendet werden. In der Regel liegt der Gehalt bei den in Wasser dispergierbaren Granulaten zwischen 10 und 90 Gew.-%.Dust-like formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight of active ingredient. In the case of granules such as dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating agents and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Färb- und Trägerstoffe, Entschäumer, Verdunstungshemmer und Mittel, die den pH-Wert oder die Viskosität beeinflussen.In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, preservatives and antifreeze agents. and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and agents which influence the pH or the viscosity.
Beispielsweise ist bekannt, daß die Wirkung von Herbiziden durch oberflächenaktive Substanzen verbessert werden kann, vorzugsweise durch Netzmittel aus der Reihe der Alkyl-polyglykolethersulfate, die beispielsweise 10 bis 18 C-Atomen enthalten und in Form ihrer Alkali- oder Ammoniumsalze, aber auch als Magnesiumsalz verwendet werden, wie Cl2/C14-Fettalkohol-diglykolethersulfat-Natrium (Genapol® LRO, Hoechst); siehe EP-A-0476555, EP-A-0048436, EP-A-0336151 oder US-A- 4,400,196 sowie Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227 - 232 (1988). Weiterhin ist bekannt, daß Alkyl-polyglykolethersulfate auch als Penetrationshilfsmittel und Wirkungsverstärker für eine Reihe anderer Herbizide, unter anderem auch für Herbizide aus der Reihe der Imidazolinone geeignet sind; siehe z.B. EP-A-0502014.For example, it is known that the action of herbicides can be improved by surface-active substances, preferably by wetting agents from the series of alkyl polyglycol ether sulfates, which contain, for example, 10 to 18 carbon atoms and are used in the form of their alkali metal or ammonium salts, but also as a magnesium salt such as C 12 / C 14 fatty alcohol diglycol ether sulfate sodium (Genapol® LRO, Hoechst); see EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). It is also known that alkyl polyglycol ether sulfates are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides from the imidazolinone series; see for example EP-A-0502014.
Die herbizide Wirkung kann auch durch die Verwendung von Pflanzenölen verstärkt werden. Unter dem Begriff Pflanzenöle werden Öle aus ölliefernden Pflanzenarten wie Sojaöl, Rapsöl, Maiskeimöl, Sonnenblumenöl, Baumwollsaatöl, Leinöl, Kokosöl, Palmöl, Distelöl oder Rhizinusöl, insbesondere Rapsöl verstanden, sowie deren Umesterungsprodukte, z.B. Alkylester wie Rapsölmethylester oder Rapsölethylester.The herbicidal effect can also be enhanced by using vegetable oils. The term vegetable oils is understood to mean oils from oil-producing plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
Die Pflanzenöle sind bevorzugt Ester von C10-C22-, vorzugsweise C12-C20-Fettsäuren. Die C10-C22-Fettsäureester sind beispielsweise Ester ungesättigter oder gesättigter C10-C22-Fettsäuren, insbesondere mit gerader Kohlenstoffatomzahl, z.B. Erucasäure, Laurinsäure, Palmitinsäure und insbesondere C18-Fettsäuren wie Stearinsäure, Ölsäure, Linolsäure oder Linolensäure.The vegetable oils are preferably esters of C 10 -C 22 , preferably C 12 -C 20 fatty acids. The C 10 -C 22 fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 fatty acids, in particular with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C 18 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
Beispiele für C10-C22-Fettsäure-Ester sind Ester, die durch Umsetzung von Glycerin oder Glykol mit den C10-C22-Fettsäuren erhalten werden, wie sie z.B. in Ölen aus ölliefernden Pflanzenarten enthalten sind, oder C C20-Alkyl-C10C22-Fettsäure-Ester, wie sie z.B. durch Umesterung der vorgenannten Glycerin- oder Glykol-C10-C22- Fettsäure-Ester mit C^C^-Alkoholen (z.B. Methanol, Ethanol, Propanol oder Butanol) erhalten werden können. Die Umesterung kann nach bekannten Methoden erfolgen, wie sie z.B. beschrieben sind im Römpp Chemie Lexikon, 9. Auflage, Band 2, Seite 1343, Thieme Verlag Stuttgart.Examples of C 10 -C 22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 fatty acids, such as those contained in oils from oil-producing plant species, or CC 20 alkyl- C 10 C 22 fatty acid esters, such as those obtained by transesterification of the above-mentioned glycerol or glycol C 10 -C 22 - Fatty acid esters with C 1 -C 4 alcohols (for example methanol, ethanol, propanol or butanol) can be obtained. The transesterification can be carried out according to known methods, as described, for example, in the Römpp Chemie Lexikon, 9th edition, volume 2, page 1343, Thieme Verlag Stuttgart.
Als C C^-Alkyl-C^-C^-Fettsäure-Ester bevorzugt sind Methylester, Ethylester, Propylester, Butylester, 2-ethyl-hexylester und Dodecylester. Als Glykol- und Glycerin-C10-C22-Fettsäure-Ester bevorzugt sind die einheitlichen oder gemischten Glykolester und Glycerinester von C10-C22-Fettsäuren, insbesondere solcher Fettsäuren mit gerader Anzahl an Kohlenstoffatomen, z.B. Erucasäure, Lauhnsäure, Palmitinsäure und insbesondere C18-Fettsäuren wie Stearinsäure, Ölsäure, Linolsäure oder Linolensäure.Preferred as CC ^ alkyl-C ^ -C ^ fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethyl-hexyl esters and dodecyl esters. Preferred as glycol and glycerol-C 10 -C 22 fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C 10 -C 22 fatty acids, in particular those fatty acids with an even number of carbon atoms, for example erucic acid, lauic acid, palmitic acid and in particular C 18 fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
Die Pflanzenöle können in den erfindungsgemäßen herbiziden Mitteln z.B. in Form kommerziell erhältlicher ölhaltiger Formulierungszusatzstoffe, insbesondere solcher auf Basis von Rapsöl wie Hasten® (Victorian Chemical Company, Australien, nachfolgend Hasten genannt, Hauptbestandteil: Rapsölethylester), Actirob®B (Novance, Frankreich, nachfolgend ActirobB genannt, Hauptbestandteil: Rapsölmethylester), Rako-Binol® (Bayer AG, Deutschland, nachfolgend Rako-Binol genannt, Hauptbestandteil: Rapsöl), Renol® (Stefes, Deutschland, nachfolgend Renol genannt, Pflanzenölbestandteil: Rapsölmethyleste) oder Stefes Mero® (Stefes, Deutschland, nachfolgend Mero genannt, Hauptbestandteil: Rapsölmethylester) enthalten sein.The vegetable oils can be used in the herbicidal compositions according to the invention e.g. in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten® (Victorian Chemical Company, Australia, hereinafter called Hasten, main constituent: rapeseed oil ethyl ester), Actirob®B (Novance, France, hereinafter referred to as ActirobB, main constituent: rapeseed oil methyl ester), Rako -Binol® (Bayer AG, Germany, hereinafter called Rako-Binol, main component: rapeseed oil), Renol® (Stefes, Germany, hereinafter referred to as Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, hereinafter referred to as Mero, main component: Rapeseed oil methyl ester) may be included.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate, sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Die Wirkstoffe können auf die Pflanzen, Pflanzenteile, Pflanzensamen oder die Anbaufläche (Ackerboden) ausgebracht werden, vorzugsweise auf die grünen Pflanzen und Pflanzenteile und gegebenenfalls zusätzlich auf den Ackerboden. Eine Möglichkeit der Anwendung ist die gemeinsame Ausbringung der Wirkstoffe in Form von Tankmischungen, wobei die optimal formulierten konzentrierten Formulierungen der Einzel Wirkstoffe gemeinsam im Tank mit Wasser gemischt und die erhaltene Spritzbrühe ausgebracht wird.For use, the formulations present in the commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground granules or granules for spreading, and sprayable solutions are usually no longer diluted with other inert substances before use. The active compounds can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil. One possible application is the joint application of the active ingredients in the form of tank mixes, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
Eine gemeinsame herbizide Formulierung der erfindungsgemäßen Kombination an Wirkstoffen (A) und (B) hat den Vorteil der leichteren Anwendbarkeit, weil die Mengen der Komponenten bereits im richtigen Verhältnis zueinander eingestellt sind. Außerdem können die Hilfsmittel in der Formulierung aufeinander optimal abgestimmt werden, während ein Tank-mix von unterschiedlichen Formulierungen unerwünschte Kombinationen von Hilfstoffen ergeben kann.A common herbicidal formulation of the combination of active compounds (A) and (B) according to the invention has the advantage of being easier to use because the amounts of the components have already been set in the correct ratio to one another. In addition, the auxiliaries in the formulation can be optimally coordinated with one another, while a tank mix of different formulations can result in undesired combinations of auxiliaries.
A. Formulierungsbeispiele allgemeiner ArtA. General wording examples
a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile eines Wirkstoffs/Wirksstoffgemischs und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.a) A dusting agent is obtained by mixing 10 parts by weight of an active ingredient / active ingredient mixture and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gew.-Teile eines Wirkstoffs/Wirksstoffgemischs, 64 Gew.-Teile kaolinhaitigen Quarz als Inertstoff, 10 Gew.-Teile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.b) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of an active substance / active substance mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium mixes as a wetting and dispersing agent and grinds in a pin mill.
c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile eines Wirkstoffs/Wirksstoffgemischs mit 6 Gew.- Teilen Alkylphenolpolyglykolether (7Triton X 207), 3 Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca. 255 bis 277EC) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (7Triton X 207) and 3 parts by weight Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277EC) are mixed and ground in a attritor to a fineness of less than 5 microns.
d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen eines Wirkstoffs/Wirksstoffgemischs, 75 Gew.-Teilen Cydohexanon als Lösemittel und 10 Gew.-Teilen oxethyliertem Nonylphenol als Emulgator.d) An emulsifiable concentrate is obtained from 15 parts by weight of an active substance / active substance mixture, 75 parts by weight of cydohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
e) Ein in Wasser dispergierbares Granulat wird erhalten indem man 75 Gew.-Teile eines Wirkstoffs/Wirksstoffgemischs,e) A water-dispersible granulate is obtained by adding 75 parts by weight of an active ingredient / active ingredient mixture,
10 Gew.-Teile ligninsulfonsaures Calcium,10 parts by weight of calcium lignosulfonate,
5 Gew.-Teile Natriumlaurylsulfat,5 parts by weight of sodium lauryl sulfate,
3 Gew.-Teile Polyvinylalkohol und3 parts by weight of polyvinyl alcohol and
7 Gew.-Teile Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert.7 parts by weight of kaolin are mixed, ground on a pin mill and the powder is granulated in a fluidized bed by spraying water as the granulating liquid.
f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man 25 Gew.-Teile eines Wirkstoffs/Wirksstoffgemischs,f) A water-dispersible granulate is also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture,
5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium,5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,
2 Gew.-Teile oleoylmethyltaurinsaures Natrium,2 parts by weight of sodium oleoylmethyl taurine,
1 Gew.-Teil Polyvinylalkohol, 17 Gew.-Teile Caiciumcarbonat und 50 Gew.-Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. B. Biologische Beispiele1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water were homogenized and pre-comminuted on a colloid mill, then ground on a bead mill and the suspension thus obtained was atomized and dried in a spray tower using a single-component nozzle. B. Biological examples
Herbizide Wirkung (Feldversuche)Herbicidal activity (field trials)
Die Samen oder Rhizomstücke von typischen Schadpflanzen wurden ausgelegt und unter natürlichen Freilandbedingungen herangezogen. Die Behandlung mit den erfindungsgemäßen Mitteln erfolgte nach dem Auflaufen der Schadpflanzen in der Regel im 2 bis 8-Blattstadium in verschiedenen Dosierungen mit einer Wasseraufwandmenge von umgerechnet 100 bis 400 l/ha.The seeds or rhizome pieces of typical harmful plants were laid out and grown under natural outdoor conditions. The treatment with the agents according to the invention was generally carried out after the emergence of the harmful plants in the 2 to 8 leaf stage in various dosages with a water application rate of the equivalent of 100 to 400 l / ha.
Nach der Anwendung (ca. 4 - 6 Wochen nach Applikation) wurde die herbizide Wirksamkeit der Wirkstoffe bzw. Wirkstoffmischungen anhand der behandelten Parzellen im Vergleich zu unbehandelten Kontroll-Parzellen visuell bonitiert. Dabei wurde Schädigung und Entwicklung aller oberirdischen Pflanzenteile erfaßt. Die Bonitierung erfolgte nach einer Prozentskala (100% Wirkung = alle Plfanzen abgestorben; 50 % Wirkung = 50% der Pflanzen und grünen Pflanzenteile abgestorben; 0 % Wirkung = keine erkennbare Wirkung = wie Kontrollparzelle). Die Boniturwerte von jeweils 4 Parzellen wurden gemittelt.After application (approx. 4-6 weeks after application), the herbicidal activity of the active ingredients or active ingredient mixtures was assessed visually on the basis of the treated plots in comparison to untreated control plots. Damage and development of all parts of the plant above ground were recorded. The ratings were given on a percentage scale (100% effect = all plants died; 50% effect = 50% of the plants and green parts of the plants died; 0% effect = no recognizable effect = like control parcel). The ratings of 4 parcels were averaged.
Die Ergebnisse sind in den nachfolgenden Tabellen angegeben, wobei in Klammern die Wirkung bei unabhängiger Anwendung der Wirkstoffe A und B angegeben ist. The results are shown in the tables below, the effect when active ingredients A and B are used independently is given in brackets.
Tabelle 1 : Herbizide WirkungTable 1: Herbicidal activity
Behandlung im 6-8 Blattstadium, Bonitierung 27 Tage nach ApplikationTreatment in the 6-8 leaf stage, rating 27 days after application
Tabelle 2: Herbizide WirkungTable 2: Herbicidal activity
Behandlung im 6-8 Blattstadium, Bonitierung 27 Tage nach Applikation Tabelle 3: Herbizide WirkungTreatment in the 6-8 leaf stage, rating 27 days after application Table 3: Herbicidal activity
Behandlung in 2 Blattstadium, Bonitierung 39 Tage nach ApplikationTreatment in 2 leaf stages, rating 39 days after application
Tabelle 4: Herbizide WirkungTable 4: Herbicidal activity
Behandlung in 6-8 Blattstadium, Bonitierung 27 Tage nach Applikation Treatment in 6-8 leaf stage, rating 27 days after application

Claims

Patentansprüche claims
1. Herbizid-Kombinationen mit einem wirksamen Gehalt an Komponenten (A) und (B), wobei1. Herbicide combinations with an effective content of components (A) and (B), wherein
(A) ein oder mehrere Herbizide aus der Gruppe der Verbindungen der Formel (I) oder deren Salzen bedeutet,(A) one or more herbicides from the group of the compounds of the formula (I) or their salts,
worinwherein
R1 Wasserstoff oder (CrC4)Alkyl,R 1 is hydrogen or (C r C 4 ) alkyl,
R2 Wasserstoff oder (CrC4)Alkyl,R 2 is hydrogen or (C r C 4 ) alkyl,
R3 Wasserstoff, (CrC4)Alkyl, (CrC4)Alkoxy, (C2-C4)Alkenoxy, (C2-C4)Alkinoxy, (C3-C6)Cycloalkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (C C4)Alkoxy und (C C4)Alkylsulfonyl substituiert ist, einer der Reste X und Y Halogen, (CrC4)Alkyl, (C1-C4)Alkoxy, (C C4)Alkylthio, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy und (C C4)Alkylthio substituiert ist, und der andere der Reste X und Y (CrC4)Alkyl, (CrC4)Alkoxy oder (CrC4)Alkylthio ist, wobei jeder der drei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy und (C,- C4)Alkylthio substituiert ist, undR 3 is hydrogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C 2 -C 4 ) alkenoxy, (C 2 -C 4 ) alkynoxy, (C 3 -C 6 ) cycloalkyl, each of which 5 last-mentioned radicals unsubstituted or substituted by one or more radicals from the group halogen, cyano, (CC 4 ) alkoxy and (CC 4 ) alkylsulfonyl, one of the radicals X and Y halogen, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (CC 4 ) alkylthio, where each of the last three radicals is unsubstituted or substituted by one or more radicals from the group halogen, (CC 4 ) alkoxy and (CC 4 ) alkylthio, and the other of the radicals X and Y is (C r C 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkylthio, each of the latter three radicals being unsubstituted or by one or more radicals from the group halogen, (CC 4 ) alkoxy and (C, - C 4 ) alkylthio is substituted, and
Z CH oder N bedeuten, undZ is CH or N, and
B) bedeutet ein oder mehrere Herbizide aus der Gruppe der Verbindungen, bestehend aus (B1 ) selektiv in einigen dikotylen Kulturen gegen monokotyle und dikotyleB) means one or more herbicides from the group of the compounds consisting of (B1) selectively in some dicotyledon crops against monocotyledons and dicotyledons
Schadpflanzen wirksamen Herbiziden, ausgewählt aus der Gruppe bestehend aus:Herbicides active against harmful plants, selected from the group consisting of:
(B1.1 ) Ethofumesate(B1.1) Ethofumesate
(B1.2) Chloridazon(B1.2) Chloridazon
(B 1.3) Triflusulfuron(B 1.3) triflusulfuron
(B1.4) Metamitron(B1.4) Metamitron
(B1.5) Metazachlor(B1.5) metazachlor
(B1.6) Napropamide(B1.6) Napropamides
(B1.7) Carbetamide(B1.7) carbetamides
(B1.8) Dimefuron(B1.8) Dimefuron
(B1.9) Dimethachlor(B1.9) Dimethachlor
(B1.10)Norflurazon(B1.10) norflurazon
(B1.11 )Fluometuron(B1.11) Fluometuron
(B 1.12)Methylarsonsäure(B 1.12) methylarsonic acid
(B1.13)Diuron(B1.13) diuron
(B1.14)Prometryn(B1.14) prometryn
(B1.15)Trifluralin(B1.15) trifluralin
(B1.16)Sulfentrazone(B1.16) sulfentrazone
(B1.17)Ethalfluralin(B1.17) ethalfluralin
(B1.18)Vernolate(B1.18) vernolate
(B1.19)Flumioxazin(B1.19) flumioxazin
(B2) selektiv in einigen dikotylen Kulturen überwiegend gegen dikotyle Schadpflanzen wirksamen Herbiziden, ausgewählt aus der Gruppe bestehend aus (B2.1 ) Desmedipham (B2.2) Phenmedipham(B2) selectively in some dicotyledon crops, herbicides active predominantly against dicotyledonous harmful plants, selected from the group consisting of (B2.1) desmedipham (B2.2) Phenmedipham
(B2.3) Quinmerac(B2.3) Quinmerac
(B2.4) Clopyralid(B2.4) Clopyralid
(B2.5) Pyridate(B2.5) pyridates
(B2.6) Ethametsulfuron-methyl(B2.6) ethametsulfuron-methyl
(B2.7) Pyrithiobac(B2.7) pyrithiobac
(B2.8) Oxyfluorfen(B2.8) oxyfluorfen
(B2.9)Fomesafen(B2.9) fomesafen
(B2.10)Flumiclorac(B2.10) flumiclorac
(B2.11 )2,4-DB(B2.11) 2,4-DB
(B2.12)Diciosulam(B2.12) Diciosulam
(B2.13)Oxasulfuron(B2.13) oxasulfuron
(B3) selektiv in einigen dikotylen Kulturen überwiegend gegen monokotyle Schadpflanzen wirksamen Herbiziden ausgewählt aus der Gruppe bestehend aus(B3) selectively in some dicot crops predominantly herbicides active against monocotyledonous harmful plants selected from the group consisting of
(B3.1 ) Profluazol (B3.2) Amicarbazone (B3.3) Pyriftalid (B3.4) Trifloxysulfuron (B3.5) Epocholeone (B3.6) Tepraloxydim(B3.1) Profluazole (B3.2) Amicarbazone (B3.3) Pyriftalid (B3.4) Trifloxysulfuron (B3.5) Epocholeone (B3.6) Tepraloxydim
2. Herbizid-Kombination nach Anspruch 1 , worin als Komponente (A) eine oder mehrere Verbindungen der Formel (A1 ) oder deren Salze, 2. Herbicide combination according to claim 1, wherein as component (A) one or more compounds of the formula (A1) or their salts,
worin R3die in Formel (I) genannte Bedeutung hat und Me = Methyl ist, enthalten ist.wherein R 3 has the meaning given in formula (I) and Me = methyl is included.
3. Herbizid-Kombinationen nach Anspruch 1 oder 2, zusätzlich enthaltend eine oder mehrere weitere Komponenten aus der Gruppe enthaltend agrochemische Wirkstoffe anderer Art, im Pflanzenschutz übliche Zusatzstoffe und Formulierungshilfsmittel.3. Herbicide combinations according to claim 1 or 2, additionally containing one or more further components from the group containing agrochemical active substances of another type, additives and formulation auxiliaries customary in crop protection.
4. Verfahren zur Bekämpfung von Schadpflanzen, worin eine Herbizid- Kombination, definiert gemäß einem oder mehreren der Ansprüche 1 bis 3, gemeinsam oder getrennt im Vorauflauf, Nachauflauf oder im Vor- und Nachauflauf auf die Pflanzen, Pflanzenteile, Pflanzensamen oder die Fläche auf der die Pflanzen wachsen appliziert wird.4. A method for controlling harmful plants, wherein a herbicide combination, defined according to one or more of claims 1 to 3, together or separately in the pre-emergence, post-emergence or in the pre-and post-emergence on the plants, parts of plants, plant seeds or the area on the the plants grow is applied.
5. Verfahren nach Anspruch 4 zur selektiven Bekämpfung von Schadpflanzen in Pflanzenkulturen.5. The method according to claim 4 for the selective control of harmful plants in plant crops.
6. Verfahren nach Anspruch 5 zur Bekämpfung von Schadpflanzen in dikotylen Pflanzenkulturen.6. The method according to claim 5 for combating harmful plants in dicotyledonous crops.
7. Verfahren nach Anspruch 5 oder 6, worin die Pflanzenkulturen gentechnisch verändert oder durch Mutationsselektion erhalten sind.7. The method according to claim 5 or 6, wherein the plant cultures are genetically modified or obtained by mutation selection.
8. Verwendung der nach einem der Ansprüche 1 bis 3 definierten Herbizid- Kombination zur Bekämpfung von Schadpflanzen. 8. Use of the herbicide combination defined according to one of claims 1 to 3 for controlling harmful plants.
EP00981250A 1999-11-15 2000-11-11 Herbicide means with acylated amino phenyl sulfonyl carbamide Expired - Lifetime EP1231839B1 (en)

Priority Applications (1)

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DE19955056A DE19955056A1 (en) 1999-11-15 1999-11-15 Herbicide combination with acylated aminophenylsulfonylureas
DE19955056 1999-11-15
PCT/EP2000/011185 WO2001035742A2 (en) 1999-11-15 2000-11-11 Herbicide means with acylated amino phenyl sulfonyl carbamide

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GB0625589D0 (en) * 2006-12-21 2007-01-31 Agrovista Uk Ltd Herbicide composition
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CN104106584A (en) * 2014-01-26 2014-10-22 山东先达农化股份有限公司 Cornfield compounded herbicide composition
CN104230762B (en) * 2014-08-28 2016-01-13 青岛农业大学 A kind of benzenesulfonamides of phosphinylidyne-containing amine group and Synthesis and applications thereof

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JPH0867604A (en) * 1994-06-23 1996-03-12 Nissan Chem Ind Ltd Herbicidal composition

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WO2001035742A2 (en) 2001-05-25
UA72013C2 (en) 2005-01-17
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YU34902A (en) 2005-07-19
HU228805B1 (en) 2013-05-28
AR026452A1 (en) 2003-02-12
SK8132002A3 (en) 2002-12-03
ES2198364T3 (en) 2004-02-01
CN1269403C (en) 2006-08-16
HRP20020516A2 (en) 2004-08-31
DE50002219D1 (en) 2003-06-18
BR0015583A (en) 2003-04-29
DE19955056A1 (en) 2001-05-17
HUP0203420A2 (en) 2003-08-28
JP5209834B2 (en) 2013-06-12
RU2273995C2 (en) 2006-04-20
JP2003513991A (en) 2003-04-15
CA2396119A1 (en) 2001-05-25
PL357474A1 (en) 2004-07-26
ATE240041T1 (en) 2003-05-15
MXPA02004896A (en) 2003-02-27
ZA200204713B (en) 2003-09-29
AU1856701A (en) 2001-05-30
PL200172B1 (en) 2008-12-31
DK1231839T3 (en) 2003-09-08
US6498126B1 (en) 2002-12-24
SK286728B6 (en) 2009-04-06
EP1231839B1 (en) 2003-05-14
CZ20022090A3 (en) 2002-10-16
WO2001035742A3 (en) 2001-12-06
HUP0203420A3 (en) 2003-10-28
HRP20020516B1 (en) 2011-04-30
BR0015583B1 (en) 2013-04-24
CA2396119C (en) 2011-05-17
PT1231839E (en) 2003-09-30
CZ297428B6 (en) 2006-12-13
CN1411338A (en) 2003-04-16

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